Montreal Canadiens vs Toronto Maple Leafs
Series timeline
▲ Montreal Canadiens ahead (peak +75)
▼ Toronto Maple Leafs ahead (peak +17)
Montreal Canadiens Toronto Arenas Toronto St. Patricks Toronto Maple Leafs Split season or tie Season with a postseason meeting One season per cell
Longest streaks: Montreal Canadiens 14 (2013-14–2016-17), Toronto Maple Leafs 12 (1939-40–1940-41). Current: Montreal Canadiens 4.
Splits
| Split | Montreal Canadiens record |
|---|---|
| Regular season | 371-318-88 |
| Postseason | 46-32 |
| Hosted by Montreal Canadiens | 256-129-43 |
| Hosted by Toronto Maple Leafs | 161-221-45 |
| Last 10 seasons (2017-18 to 2026-27) | 20-28 |
| Largest Montreal Canadiens win | 11-0 (1943-44) |
| Largest Toronto Maple Leafs win | 11-3 (1918-19) |
Postseason meetings
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 2020-21 | May 31, 2021 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | |
| 2020-21 | May 29, 2021 | Montreal Canadiens | 3-2 | at Montreal Canadiens | |
| 2020-21 | May 27, 2021 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | |
| 2020-21 | May 25, 2021 | Toronto Maple Leafs | 4-0 | at Montreal Canadiens | |
| 2020-21 | May 24, 2021 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | |
| 2020-21 | May 22, 2021 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | |
| 2020-21 | May 20, 2021 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | |
| 1978-79 | Apr 22, 1979 | Montreal Canadiens | 5-4 | at Toronto Maple Leafs | |
| 1978-79 | Apr 21, 1979 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | |
| 1978-79 | Apr 18, 1979 | Montreal Canadiens | 5-1 | at Montreal Canadiens | |
| 1978-79 | Apr 16, 1979 | Montreal Canadiens | 5-2 | at Montreal Canadiens | |
| 1977-78 | May 9, 1978 | Montreal Canadiens | 2-0 | at Toronto Maple Leafs | |
| 1977-78 | May 6, 1978 | Montreal Canadiens | 6-1 | at Toronto Maple Leafs | |
| 1977-78 | May 4, 1978 | Montreal Canadiens | 3-2 | at Montreal Canadiens | |
| 1977-78 | May 2, 1978 | Montreal Canadiens | 5-3 | at Montreal Canadiens | |
| 1966-67 | May 2, 1967 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | |
| 1966-67 | Apr 29, 1967 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | |
| 1966-67 | Apr 27, 1967 | Montreal Canadiens | 6-2 | at Toronto Maple Leafs | |
| 1966-67 | Apr 25, 1967 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| 1966-67 | Apr 22, 1967 | Toronto Maple Leafs | 3-0 | at Montreal Canadiens | |
| 1966-67 | Apr 20, 1967 | Montreal Canadiens | 6-2 | at Montreal Canadiens | |
| 1965-66 | Apr 14, 1966 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | |
| 1965-66 | Apr 12, 1966 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | |
| 1965-66 | Apr 9, 1966 | Montreal Canadiens | 2-0 | at Montreal Canadiens | |
| 1965-66 | Apr 7, 1966 | Montreal Canadiens | 4-3 | at Montreal Canadiens | |
| 1964-65 | Apr 13, 1965 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | |
| 1964-65 | Apr 10, 1965 | Montreal Canadiens | 3-1 | at Montreal Canadiens | |
| 1964-65 | Apr 8, 1965 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | |
| 1964-65 | Apr 6, 1965 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| 1964-65 | Apr 3, 1965 | Montreal Canadiens | 3-1 | at Montreal Canadiens | |
| 1964-65 | Apr 1, 1965 | Montreal Canadiens | 3-2 | at Montreal Canadiens | |
| 1963-64 | Apr 9, 1964 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | |
| 1963-64 | Apr 7, 1964 | Toronto Maple Leafs | 3-0 | at Toronto Maple Leafs | |
| 1963-64 | Apr 4, 1964 | Montreal Canadiens | 4-2 | at Montreal Canadiens | |
| 1963-64 | Apr 2, 1964 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | |
| 1963-64 | Mar 31, 1964 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | |
| 1963-64 | Mar 28, 1964 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | |
| 1963-64 | Mar 26, 1964 | Montreal Canadiens | 2-0 | at Montreal Canadiens | |
| 1962-63 | Apr 4, 1963 | Toronto Maple Leafs | 5-0 | at Toronto Maple Leafs | |
| 1962-63 | Apr 2, 1963 | Montreal Canadiens | 3-1 | at Montreal Canadiens | |
| 1962-63 | Mar 30, 1963 | Toronto Maple Leafs | 2-0 | at Montreal Canadiens | |
| 1962-63 | Mar 28, 1963 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| 1962-63 | Mar 26, 1963 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | |
| 1959-60 | Apr 14, 1960 | Montreal Canadiens | 4-0 | at Toronto Maple Leafs | |
| 1959-60 | Apr 12, 1960 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | |
| 1959-60 | Apr 9, 1960 | Montreal Canadiens | 2-1 | at Montreal Canadiens | |
| 1959-60 | Apr 7, 1960 | Montreal Canadiens | 4-2 | at Montreal Canadiens | |
| 1958-59 | Apr 18, 1959 | Montreal Canadiens | 5-3 | at Montreal Canadiens | |
| 1958-59 | Apr 16, 1959 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | |
| 1958-59 | Apr 14, 1959 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| 1958-59 | Apr 11, 1959 | Montreal Canadiens | 3-1 | at Montreal Canadiens | |
| 1958-59 | Apr 9, 1959 | Montreal Canadiens | 5-3 | at Montreal Canadiens | |
| 1950-51 | Apr 21, 1951 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| 1950-51 | Apr 19, 1951 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | |
| 1950-51 | Apr 17, 1951 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | |
| 1950-51 | Apr 14, 1951 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | |
| 1950-51 | Apr 11, 1951 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| 1946-47 | Apr 19, 1947 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | |
| 1946-47 | Apr 17, 1947 | Montreal Canadiens | 3-1 | at Montreal Canadiens | |
| 1946-47 | Apr 15, 1947 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | |
| 1946-47 | Apr 12, 1947 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | |
| 1946-47 | Apr 10, 1947 | Toronto Maple Leafs | 4-0 | at Montreal Canadiens | |
| 1946-47 | Apr 8, 1947 | Montreal Canadiens | 6-0 | at Montreal Canadiens | |
| 1944-45 | Mar 31, 1945 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| 1944-45 | Mar 29, 1945 | Montreal Canadiens | 10-3 | at Montreal Canadiens | |
| 1944-45 | Mar 27, 1945 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | |
| 1944-45 | Mar 24, 1945 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | |
| 1944-45 | Mar 22, 1945 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | |
| 1944-45 | Mar 20, 1945 | Toronto Maple Leafs | 1-0 | at Montreal Canadiens | |
| 1943-44 | Mar 30, 1944 | Montreal Canadiens | 11-0 | at Montreal Canadiens | |
| 1943-44 | Mar 28, 1944 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | |
| 1943-44 | Mar 25, 1944 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | |
| 1943-44 | Mar 23, 1944 | Montreal Canadiens | 5-1 | at Montreal Canadiens | |
| 1943-44 | Mar 21, 1944 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | |
| 1924-25 | Mar 13, 1925 | Montreal Canadiens | 2-0 | at Toronto St. Patricks | |
| 1924-25 | Mar 11, 1925 | Montreal Canadiens | 3-2 | at Montreal Canadiens | |
| 1917-18 | Mar 13, 1918 | Montreal Canadiens | 4-3 | at Montreal Canadiens | |
| 1917-18 | Mar 11, 1918 | Toronto Arenas | 7-3 | at Toronto Arenas |
In the record book
- Longest winning streaks#16 in NHL
- Longest active streaks#71 in NHL
- Most lead changes#30 in NHL
- Biggest blowouts#21 in NHL
Every meeting
2020s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 2026-27 | Sep 29, 2026 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | |
| 2025-26 (3-1) | Oct 8, 2025 | Toronto Maple Leafs | 5-2 | at Toronto Maple Leafs | |
| Nov 22, 2025 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Dec 6, 2025 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Mar 10, 2026 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| 2024-25 (1-3) | Oct 9, 2024 | Montreal Canadiens | 1-0 | at Montreal Canadiens | |
| Nov 9, 2024 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | ||
| Jan 18, 2025 | Toronto Maple Leafs | 7-3 | at Montreal Canadiens | ||
| Apr 12, 2025 | Toronto Maple Leafs | 1-0 | at Toronto Maple Leafs | ||
| 2023-24 (0-3) | Oct 11, 2023 | Toronto Maple Leafs | 6-5 | at Toronto Maple Leafs | |
| Mar 9, 2024 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Apr 6, 2024 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| 2022-23 (2-2) | Oct 12, 2022 | Montreal Canadiens | 4-3 | at Montreal Canadiens | |
| Jan 21, 2023 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Feb 18, 2023 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | ||
| Apr 8, 2023 | Toronto Maple Leafs | 7-1 | at Toronto Maple Leafs | ||
| 2021-22 (2-2) | Oct 13, 2021 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | |
| Feb 21, 2022 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Mar 26, 2022 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Apr 9, 2022 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| 2020-21 (7-10) | Jan 13, 2021 | Toronto Maple Leafs | 5-4 | at Toronto Maple Leafs | |
| Feb 10, 2021 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Feb 13, 2021 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Feb 20, 2021 | Toronto Maple Leafs | 5-3 | at Montreal Canadiens | ||
| Apr 7, 2021 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Apr 12, 2021 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Apr 28, 2021 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | ||
| May 3, 2021 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| May 6, 2021 | Toronto Maple Leafs | 5-2 | at Toronto Maple Leafs | ||
| May 8, 2021 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| May 20, 2021 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | Postseason | |
| May 22, 2021 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | Postseason | |
| May 24, 2021 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | Postseason | |
| May 25, 2021 | Toronto Maple Leafs | 4-0 | at Montreal Canadiens | Postseason | |
| May 27, 2021 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | Postseason | |
| May 29, 2021 | Montreal Canadiens | 3-2 | at Montreal Canadiens | Postseason | |
| May 31, 2021 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | Postseason |
2010s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 2019-20 (3-0) | Oct 5, 2019 | Montreal Canadiens | 6-5 | at Toronto Maple Leafs | |
| Oct 26, 2019 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Feb 8, 2020 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| 2018-19 (1-3) | Oct 3, 2018 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| Feb 9, 2019 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | ||
| Feb 23, 2019 | Toronto Maple Leafs | 6-3 | at Toronto Maple Leafs | ||
| Apr 6, 2019 | Montreal Canadiens | 6-5 | at Montreal Canadiens | ||
| 2017-18 (0-4) | Oct 14, 2017 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | |
| Nov 18, 2017 | Toronto Maple Leafs | 6-0 | at Montreal Canadiens | ||
| Mar 17, 2018 | Toronto Maple Leafs | 4-0 | at Toronto Maple Leafs | ||
| Apr 7, 2018 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| 2016-17 (4-0) | Oct 29, 2016 | Montreal Canadiens | 2-1 | at Montreal Canadiens | |
| Nov 19, 2016 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Jan 7, 2017 | Montreal Canadiens | 5-3 | at Toronto Maple Leafs | ||
| Feb 25, 2017 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| 2015-16 (4-0) | Oct 7, 2015 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | |
| Oct 24, 2015 | Montreal Canadiens | 5-3 | at Montreal Canadiens | ||
| Jan 23, 2016 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Feb 27, 2016 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| 2014-15 (4-0) | Oct 8, 2014 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | |
| Feb 14, 2015 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Feb 28, 2015 | Montreal Canadiens | 4-0 | at Montreal Canadiens | ||
| Apr 11, 2015 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| 2013-14 (3-2) | Oct 1, 2013 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | |
| Nov 30, 2013 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Jan 18, 2014 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | ||
| Mar 1, 2014 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| Mar 22, 2014 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| 2012-13 (2-3) | Jan 19, 2013 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | |
| Feb 9, 2013 | Toronto Maple Leafs | 6-0 | at Montreal Canadiens | ||
| Feb 27, 2013 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | ||
| Apr 13, 2013 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | ||
| Apr 27, 2013 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| 2011-12 (3-3) | Oct 6, 2011 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | |
| Oct 22, 2011 | Toronto Maple Leafs | 5-4 | at Montreal Canadiens | ||
| Jan 21, 2012 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Feb 11, 2012 | Montreal Canadiens | 5-0 | at Toronto Maple Leafs | ||
| Mar 3, 2012 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Apr 7, 2012 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| 2010-11 (3-3) | Oct 7, 2010 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| Nov 20, 2010 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Dec 11, 2010 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 12, 2011 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Feb 24, 2011 | Toronto Maple Leafs | 5-4 | at Montreal Canadiens | ||
| Apr 9, 2011 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs |
2000s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 2009-10 (3-3) | Oct 1, 2009 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | |
| Oct 31, 2009 | Montreal Canadiens | 5-4 | at Montreal Canadiens | ||
| Dec 1, 2009 | Toronto Maple Leafs | 3-0 | at Montreal Canadiens | ||
| Dec 26, 2009 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Mar 20, 2010 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Apr 10, 2010 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | ||
| 2008-09 (3-3) | Oct 11, 2008 | Montreal Canadiens | 6-1 | at Toronto Maple Leafs | |
| Nov 8, 2008 | Toronto Maple Leafs | 6-3 | at Toronto Maple Leafs | ||
| Jan 8, 2009 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| Feb 7, 2009 | Toronto Maple Leafs | 5-2 | at Montreal Canadiens | ||
| Mar 21, 2009 | Toronto Maple Leafs | 5-2 | at Montreal Canadiens | ||
| Apr 4, 2009 | Montreal Canadiens | 6-2 | at Toronto Maple Leafs | ||
| 2007-08 (4-4) | Oct 6, 2007 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | |
| Nov 3, 2007 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Nov 13, 2007 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| Nov 27, 2007 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| Dec 15, 2007 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Feb 7, 2008 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Mar 29, 2008 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Apr 5, 2008 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| 2006-07 (4-4) | Oct 7, 2006 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | |
| Oct 28, 2006 | Toronto Maple Leafs | 5-4 | at Montreal Canadiens | ||
| Nov 11, 2006 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | ||
| Dec 2, 2006 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| Jan 27, 2007 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | ||
| Feb 26, 2007 | Montreal Canadiens | 5-4 | at Montreal Canadiens | ||
| Mar 17, 2007 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Apr 7, 2007 | Toronto Maple Leafs | 6-5 | at Toronto Maple Leafs | ||
| 2005-06 (4-4) | Oct 8, 2005 | Montreal Canadiens | 5-4 | at Toronto Maple Leafs | |
| Oct 15, 2005 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Nov 12, 2005 | Toronto Maple Leafs | 5-4 | at Montreal Canadiens | ||
| Nov 26, 2005 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | ||
| Jan 28, 2006 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| Mar 7, 2006 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | ||
| Mar 23, 2006 | Montreal Canadiens | 5-1 | at Montreal Canadiens | ||
| Mar 25, 2006 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| 2003-04 (2-4) | Oct 11, 2003 | Montreal Canadiens | 4-0 | at Toronto Maple Leafs | |
| Oct 18, 2003 | Toronto Maple Leafs | 1-0 | at Montreal Canadiens | ||
| Dec 20, 2003 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Jan 24, 2004 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | ||
| Feb 21, 2004 | Toronto Maple Leafs | 5-4 | at Toronto Maple Leafs | ||
| Mar 13, 2004 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| 2002-03 (1-3-1) | Oct 19, 2002 | Tie | 2-2 | at Montreal Canadiens | |
| Nov 2, 2002 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | ||
| Jan 18, 2003 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Feb 8, 2003 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 22, 2003 | Toronto Maple Leafs | 5-3 | at Montreal Canadiens | ||
| 2001-02 (0-2-3) | Oct 6, 2001 | Tie | 2-2 | at Montreal Canadiens | |
| Dec 15, 2001 | Toronto Maple Leafs | 6-4 | at Toronto Maple Leafs | ||
| Jan 12, 2002 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Feb 9, 2002 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | ||
| Mar 9, 2002 | Tie | 1-1 | at Montreal Canadiens | ||
| 2000-01 (1-4) | Oct 7, 2000 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | |
| Nov 18, 2000 | Toronto Maple Leafs | 6-1 | at Montreal Canadiens | ||
| Dec 23, 2000 | Toronto Maple Leafs | 5-2 | at Montreal Canadiens | ||
| Feb 24, 2001 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | ||
| Mar 31, 2001 | Montreal Canadiens | 4-1 | at Montreal Canadiens |
1990s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1999-00 (1-4) | Oct 2, 1999 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | |
| Oct 23, 1999 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Dec 18, 1999 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Feb 19, 2000 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Mar 4, 2000 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | ||
| 1998-99 (3-2) | Dec 5, 1998 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | |
| Dec 26, 1998 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Feb 20, 1999 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Mar 13, 1999 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Apr 17, 1999 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| 1997-98 (1-1) | Nov 1, 1997 | Montreal Canadiens | 5-1 | at Montreal Canadiens | |
| Feb 28, 1998 | Toronto Maple Leafs | 4-0 | at Toronto Maple Leafs | ||
| 1996-97 (1-1) | Nov 23, 1996 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | |
| Feb 22, 1997 | Toronto Maple Leafs | 5-1 | at Montreal Canadiens | ||
| 1995-96 (2-0) | Oct 21, 1995 | Montreal Canadiens | 4-3 | at Montreal Canadiens | |
| Feb 3, 1996 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| 1993-94 (2-0) | Oct 30, 1993 | Montreal Canadiens | 5-2 | at Montreal Canadiens | |
| Feb 26, 1994 | Montreal Canadiens | 3-0 | at Toronto Maple Leafs | ||
| 1992-93 (0-2) | Jan 9, 1993 | Toronto Maple Leafs | 5-4 | at Montreal Canadiens | |
| Jan 23, 1993 | Toronto Maple Leafs | 4-0 | at Toronto Maple Leafs | ||
| 1991-92 (2-1) | Oct 3, 1991 | Montreal Canadiens | 4-3 | at Montreal Canadiens | |
| Dec 9, 1991 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| Feb 8, 1992 | Toronto Maple Leafs | 6-4 | at Toronto Maple Leafs | ||
| 1990-91 (1-1-1) | Dec 12, 1990 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | |
| Jan 23, 1991 | Montreal Canadiens | 7-3 | at Montreal Canadiens | ||
| Feb 23, 1991 | Tie | 3-3 | at Montreal Canadiens |
1980s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1989-90 (2-1) | Nov 18, 1989 | Montreal Canadiens | 4-3 | at Montreal Canadiens | |
| Dec 9, 1989 | Toronto Maple Leafs | 7-4 | at Toronto Maple Leafs | ||
| Jan 27, 1990 | Montreal Canadiens | 5-3 | at Toronto Maple Leafs | ||
| 1988-89 (2-1) | Oct 17, 1988 | Toronto Maple Leafs | 6-2 | at Montreal Canadiens | |
| Jan 14, 1989 | Montreal Canadiens | 5-3 | at Toronto Maple Leafs | ||
| Jan 21, 1989 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| 1987-88 (3-0) | Oct 21, 1987 | Montreal Canadiens | 10-3 | at Toronto Maple Leafs | |
| Nov 9, 1987 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Dec 26, 1987 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| 1986-87 (2-1) | Oct 9, 1986 | Toronto Maple Leafs | 7-4 | at Toronto Maple Leafs | |
| Jan 12, 1987 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Mar 21, 1987 | Montreal Canadiens | 9-4 | at Montreal Canadiens | ||
| 1985-86 (2-1) | Dec 7, 1985 | Montreal Canadiens | 6-3 | at Toronto Maple Leafs | |
| Jan 1, 1986 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Jan 25, 1986 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| 1984-85 (0-3) | Nov 19, 1984 | Toronto Maple Leafs | 6-4 | at Montreal Canadiens | |
| Feb 9, 1985 | Toronto Maple Leafs | 6-2 | at Montreal Canadiens | ||
| Feb 10, 1985 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| 1983-84 (2-1) | Oct 22, 1983 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | |
| Jan 11, 1984 | Montreal Canadiens | 6-4 | at Toronto Maple Leafs | ||
| Mar 17, 1984 | Montreal Canadiens | 6-1 | at Montreal Canadiens | ||
| 1982-83 (0-1-2) | Dec 28, 1982 | Tie | 4-4 | at Montreal Canadiens | |
| Dec 29, 1982 | Toronto Maple Leafs | 6-5 | at Toronto Maple Leafs | ||
| Mar 8, 1983 | Tie | 3-3 | at Montreal Canadiens | ||
| 1981-82 (2-0-1) | Dec 12, 1981 | Montreal Canadiens | 6-2 | at Toronto Maple Leafs | |
| Feb 27, 1982 | Tie | 3-3 | at Montreal Canadiens | ||
| Mar 6, 1982 | Montreal Canadiens | 6-1 | at Toronto Maple Leafs | ||
| 1980-81 (3-1) | Nov 19, 1980 | Montreal Canadiens | 5-4 | at Toronto Maple Leafs | |
| Dec 11, 1980 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Jan 17, 1981 | Toronto Maple Leafs | 6-5 | at Toronto Maple Leafs | ||
| Feb 28, 1981 | Montreal Canadiens | 5-3 | at Montreal Canadiens |
1970s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1979-80 (3-1) | Dec 5, 1979 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| Dec 23, 1979 | Montreal Canadiens | 8-4 | at Montreal Canadiens | ||
| Jan 9, 1980 | Montreal Canadiens | 5-3 | at Toronto Maple Leafs | ||
| Jan 19, 1980 | Montreal Canadiens | 7-2 | at Montreal Canadiens | ||
| 1978-79 (7-0-1) | Oct 25, 1978 | Tie | 4-4 | at Toronto Maple Leafs | |
| Nov 11, 1978 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Feb 3, 1979 | Montreal Canadiens | 6-3 | at Toronto Maple Leafs | ||
| Mar 1, 1979 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Apr 16, 1979 | Montreal Canadiens | 5-2 | at Montreal Canadiens | Postseason | |
| Apr 18, 1979 | Montreal Canadiens | 5-1 | at Montreal Canadiens | Postseason | |
| Apr 21, 1979 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | Postseason | |
| Apr 22, 1979 | Montreal Canadiens | 5-4 | at Toronto Maple Leafs | Postseason | |
| 1977-78 (8-0-1) | Oct 26, 1977 | Tie | 2-2 | at Toronto Maple Leafs | |
| Nov 12, 1977 | Montreal Canadiens | 5-0 | at Montreal Canadiens | ||
| Dec 21, 1977 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Mar 9, 1978 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Apr 5, 1978 | Montreal Canadiens | 6-3 | at Toronto Maple Leafs | ||
| May 2, 1978 | Montreal Canadiens | 5-3 | at Montreal Canadiens | Postseason | |
| May 4, 1978 | Montreal Canadiens | 3-2 | at Montreal Canadiens | Postseason | |
| May 6, 1978 | Montreal Canadiens | 6-1 | at Toronto Maple Leafs | Postseason | |
| May 9, 1978 | Montreal Canadiens | 2-0 | at Toronto Maple Leafs | Postseason | |
| 1976-77 (2-1-2) | Oct 21, 1976 | Montreal Canadiens | 5-3 | at Montreal Canadiens | |
| Nov 17, 1976 | Toronto Maple Leafs | 1-0 | at Toronto Maple Leafs | ||
| Nov 21, 1976 | Montreal Canadiens | 9-5 | at Montreal Canadiens | ||
| Mar 9, 1977 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Mar 30, 1977 | Tie | 3-3 | at Montreal Canadiens | ||
| 1975-76 (3-1-1) | Nov 22, 1975 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | |
| Dec 10, 1975 | Tie | 3-3 | at Montreal Canadiens | ||
| Jan 11, 1976 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Feb 18, 1976 | Montreal Canadiens | 7-5 | at Toronto Maple Leafs | ||
| Mar 24, 1976 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| 1974-75 (1-2-2) | Oct 23, 1974 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | |
| Jan 18, 1975 | Toronto Maple Leafs | 5-3 | at Montreal Canadiens | ||
| Feb 12, 1975 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Mar 12, 1975 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Mar 22, 1975 | Toronto Maple Leafs | 6-4 | at Montreal Canadiens | ||
| 1973-74 (2-3) | Oct 17, 1973 | Toronto Maple Leafs | 5-3 | at Montreal Canadiens | |
| Nov 7, 1973 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| Dec 26, 1973 | Toronto Maple Leafs | 9-2 | at Toronto Maple Leafs | ||
| Jan 23, 1974 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| Apr 3, 1974 | Toronto Maple Leafs | 5-3 | at Montreal Canadiens | ||
| 1972-73 (5-0-1) | Oct 11, 1972 | Tie | 2-2 | at Toronto Maple Leafs | |
| Nov 8, 1972 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Jan 3, 1973 | Montreal Canadiens | 8-4 | at Toronto Maple Leafs | ||
| Jan 27, 1973 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Feb 18, 1973 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Mar 7, 1973 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| 1971-72 (4-1-1) | Nov 10, 1971 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | |
| Dec 22, 1971 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Jan 1, 1972 | Toronto Maple Leafs | 5-2 | at Toronto Maple Leafs | ||
| Jan 19, 1972 | Montreal Canadiens | 1-0 | at Montreal Canadiens | ||
| Mar 15, 1972 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | ||
| Mar 22, 1972 | Tie | 3-3 | at Montreal Canadiens | ||
| 1970-71 (2-4) | Oct 28, 1970 | Toronto Maple Leafs | 6-2 | at Toronto Maple Leafs | |
| Nov 19, 1970 | Montreal Canadiens | 5-1 | at Montreal Canadiens | ||
| Dec 9, 1970 | Toronto Maple Leafs | 4-0 | at Toronto Maple Leafs | ||
| Jan 30, 1971 | Toronto Maple Leafs | 5-4 | at Montreal Canadiens | ||
| Mar 10, 1971 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Mar 18, 1971 | Montreal Canadiens | 4-1 | at Montreal Canadiens |
1960s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1969-70 (4-1-3) | Oct 15, 1969 | Tie | 2-2 | at Toronto Maple Leafs | |
| Nov 8, 1969 | Montreal Canadiens | 6-3 | at Montreal Canadiens | ||
| Nov 26, 1969 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Dec 10, 1969 | Montreal Canadiens | 6-3 | at Montreal Canadiens | ||
| Feb 11, 1970 | Tie | 3-3 | at Montreal Canadiens | ||
| Feb 18, 1970 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | ||
| Mar 15, 1970 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Mar 25, 1970 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| 1968-69 (4-3-1) | Oct 30, 1968 | Montreal Canadiens | 5-0 | at Toronto Maple Leafs | |
| Nov 14, 1968 | Toronto Maple Leafs | 5-3 | at Montreal Canadiens | ||
| Dec 11, 1968 | Tie | 4-4 | at Toronto Maple Leafs | ||
| Dec 26, 1968 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Feb 19, 1969 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | ||
| Feb 20, 1969 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Mar 6, 1969 | Montreal Canadiens | 5-3 | at Montreal Canadiens | ||
| Mar 26, 1969 | Toronto Maple Leafs | 6-4 | at Toronto Maple Leafs | ||
| 1967-68 (5-3-2) | Oct 19, 1967 | Montreal Canadiens | 1-0 | at Montreal Canadiens | |
| Nov 1, 1967 | Toronto Maple Leafs | 5-0 | at Toronto Maple Leafs | ||
| Nov 29, 1967 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Dec 20, 1967 | Montreal Canadiens | 5-0 | at Montreal Canadiens | ||
| Dec 27, 1967 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Jan 3, 1968 | Tie | 1-1 | at Montreal Canadiens | ||
| Jan 30, 1968 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Feb 14, 1968 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Mar 20, 1968 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Mar 27, 1968 | Toronto Maple Leafs | 6-0 | at Toronto Maple Leafs | ||
| 1966-67 (8-10-2) | Nov 2, 1966 | Tie | 2-2 | at Toronto Maple Leafs | |
| Nov 9, 1966 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Nov 19, 1966 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | ||
| Nov 30, 1966 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Dec 7, 1966 | Montreal Canadiens | 6-3 | at Montreal Canadiens | ||
| Dec 21, 1966 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| Jan 11, 1967 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| Jan 25, 1967 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Feb 1, 1967 | Montreal Canadiens | 7-1 | at Montreal Canadiens | ||
| Feb 22, 1967 | Toronto Maple Leafs | 5-2 | at Toronto Maple Leafs | ||
| Mar 1, 1967 | Tie | 1-1 | at Montreal Canadiens | ||
| Mar 8, 1967 | Toronto Maple Leafs | 6-4 | at Toronto Maple Leafs | ||
| Mar 22, 1967 | Montreal Canadiens | 5-3 | at Toronto Maple Leafs | ||
| Mar 29, 1967 | Montreal Canadiens | 5-3 | at Montreal Canadiens | ||
| Apr 20, 1967 | Montreal Canadiens | 6-2 | at Montreal Canadiens | Postseason | |
| Apr 22, 1967 | Toronto Maple Leafs | 3-0 | at Montreal Canadiens | Postseason | |
| Apr 25, 1967 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | Postseason | |
| Apr 27, 1967 | Montreal Canadiens | 6-2 | at Toronto Maple Leafs | Postseason | |
| Apr 29, 1967 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | Postseason | |
| May 2, 1967 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | Postseason | |
| 1965-66 (9-7-2) | Nov 4, 1965 | Montreal Canadiens | 5-1 | at Montreal Canadiens | |
| Nov 10, 1965 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Nov 18, 1965 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Nov 24, 1965 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Dec 16, 1965 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Dec 29, 1965 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Jan 13, 1966 | Toronto Maple Leafs | 6-0 | at Montreal Canadiens | ||
| Feb 3, 1966 | Montreal Canadiens | 5-4 | at Montreal Canadiens | ||
| Feb 16, 1966 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Mar 2, 1966 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Mar 3, 1966 | Toronto Maple Leafs | 4-0 | at Montreal Canadiens | ||
| Mar 16, 1966 | Montreal Canadiens | 7-2 | at Toronto Maple Leafs | ||
| Mar 24, 1966 | Toronto Maple Leafs | 2-0 | at Montreal Canadiens | ||
| Mar 30, 1966 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Apr 7, 1966 | Montreal Canadiens | 4-3 | at Montreal Canadiens | Postseason | |
| Apr 9, 1966 | Montreal Canadiens | 2-0 | at Montreal Canadiens | Postseason | |
| Apr 12, 1966 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | Postseason | |
| Apr 14, 1966 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | Postseason | |
| 1964-65 (10-7-3) | Oct 28, 1964 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | |
| Nov 5, 1964 | Tie | 2-2 | at Montreal Canadiens | ||
| Nov 18, 1964 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Dec 3, 1964 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Dec 9, 1964 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Dec 17, 1964 | Tie | 2-2 | at Montreal Canadiens | ||
| Dec 30, 1964 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| Jan 14, 1965 | Toronto Maple Leafs | 5-3 | at Montreal Canadiens | ||
| Jan 20, 1965 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Feb 4, 1965 | Toronto Maple Leafs | 5-2 | at Montreal Canadiens | ||
| Feb 10, 1965 | Toronto Maple Leafs | 6-2 | at Toronto Maple Leafs | ||
| Mar 4, 1965 | Tie | 2-2 | at Montreal Canadiens | ||
| Mar 18, 1965 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Mar 24, 1965 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Apr 1, 1965 | Montreal Canadiens | 3-2 | at Montreal Canadiens | Postseason | |
| Apr 3, 1965 | Montreal Canadiens | 3-1 | at Montreal Canadiens | Postseason | |
| Apr 6, 1965 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | Postseason | |
| Apr 8, 1965 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | Postseason | |
| Apr 10, 1965 | Montreal Canadiens | 3-1 | at Montreal Canadiens | Postseason | |
| Apr 13, 1965 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | Postseason | |
| 1963-64 (10-9-2) | Oct 16, 1963 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | |
| Oct 30, 1963 | Toronto Maple Leafs | 6-3 | at Toronto Maple Leafs | ||
| Nov 13, 1963 | Tie | 2-2 | at Montreal Canadiens | ||
| Nov 20, 1963 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Dec 4, 1963 | Toronto Maple Leafs | 3-0 | at Toronto Maple Leafs | ||
| Dec 18, 1963 | Montreal Canadiens | 7-3 | at Montreal Canadiens | ||
| Jan 8, 1964 | Toronto Maple Leafs | 6-1 | at Toronto Maple Leafs | ||
| Jan 22, 1964 | Montreal Canadiens | 3-0 | at Toronto Maple Leafs | ||
| Jan 29, 1964 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Feb 5, 1964 | Montreal Canadiens | 2-0 | at Toronto Maple Leafs | ||
| Feb 12, 1964 | Montreal Canadiens | 4-0 | at Montreal Canadiens | ||
| Feb 26, 1964 | Montreal Canadiens | 1-0 | at Montreal Canadiens | ||
| Mar 11, 1964 | Toronto Maple Leafs | 1-0 | at Toronto Maple Leafs | ||
| Mar 18, 1964 | Tie | 2-2 | at Montreal Canadiens | ||
| Mar 26, 1964 | Montreal Canadiens | 2-0 | at Montreal Canadiens | Postseason | |
| Mar 28, 1964 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | Postseason | |
| Mar 31, 1964 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | Postseason | |
| Apr 2, 1964 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | Postseason | |
| Apr 4, 1964 | Montreal Canadiens | 4-2 | at Montreal Canadiens | Postseason | |
| Apr 7, 1964 | Toronto Maple Leafs | 3-0 | at Toronto Maple Leafs | Postseason | |
| Apr 9, 1964 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | Postseason | |
| 1962-63 (4-10-5) | Oct 18, 1962 | Montreal Canadiens | 4-2 | at Montreal Canadiens | |
| Oct 31, 1962 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| Nov 1, 1962 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Nov 14, 1962 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Nov 29, 1962 | Tie | 4-4 | at Montreal Canadiens | ||
| Dec 5, 1962 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Dec 20, 1962 | Tie | 4-4 | at Montreal Canadiens | ||
| Jan 17, 1963 | Montreal Canadiens | 6-4 | at Montreal Canadiens | ||
| Jan 23, 1963 | Toronto Maple Leafs | 5-1 | at Toronto Maple Leafs | ||
| Jan 31, 1963 | Toronto Maple Leafs | 6-3 | at Montreal Canadiens | ||
| Feb 9, 1963 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Feb 20, 1963 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Mar 14, 1963 | Tie | 3-3 | at Montreal Canadiens | ||
| Mar 20, 1963 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Mar 26, 1963 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | Postseason | |
| Mar 28, 1963 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | Postseason | |
| Mar 30, 1963 | Toronto Maple Leafs | 2-0 | at Montreal Canadiens | Postseason | |
| Apr 2, 1963 | Montreal Canadiens | 3-1 | at Montreal Canadiens | Postseason | |
| Apr 4, 1963 | Toronto Maple Leafs | 5-0 | at Toronto Maple Leafs | Postseason | |
| 1961-62 (7-4-3) | Nov 1, 1961 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | |
| Nov 9, 1961 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Nov 15, 1961 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Nov 29, 1961 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Nov 30, 1961 | Tie | 1-1 | at Montreal Canadiens | ||
| Dec 7, 1961 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Jan 3, 1962 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Jan 11, 1962 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Feb 1, 1962 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Feb 10, 1962 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Feb 21, 1962 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Mar 8, 1962 | Tie | 1-1 | at Montreal Canadiens | ||
| Mar 14, 1962 | Toronto Maple Leafs | 5-2 | at Toronto Maple Leafs | ||
| Mar 22, 1962 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| 1960-61 (8-6) | Oct 6, 1960 | Montreal Canadiens | 5-0 | at Montreal Canadiens | |
| Oct 19, 1960 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Nov 3, 1960 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Nov 19, 1960 | Toronto Maple Leafs | 6-3 | at Toronto Maple Leafs | ||
| Dec 1, 1960 | Montreal Canadiens | 6-3 | at Montreal Canadiens | ||
| Dec 7, 1960 | Montreal Canadiens | 6-2 | at Toronto Maple Leafs | ||
| Dec 15, 1960 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Dec 28, 1960 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| Jan 12, 1961 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| Jan 25, 1961 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | ||
| Feb 15, 1961 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Feb 23, 1961 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Mar 1, 1961 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Mar 16, 1961 | Montreal Canadiens | 5-2 | at Montreal Canadiens |
1950s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1959-60 (14-3-1) | Oct 15, 1959 | Montreal Canadiens | 4-2 | at Montreal Canadiens | |
| Oct 28, 1959 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Nov 12, 1959 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Nov 21, 1959 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| Dec 2, 1959 | Toronto Maple Leafs | 1-0 | at Toronto Maple Leafs | ||
| Dec 17, 1959 | Montreal Canadiens | 8-2 | at Montreal Canadiens | ||
| Dec 30, 1959 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Jan 14, 1960 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Feb 4, 1960 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Feb 10, 1960 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Feb 24, 1960 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Mar 3, 1960 | Montreal Canadiens | 5-1 | at Montreal Canadiens | ||
| Mar 9, 1960 | Montreal Canadiens | 9-4 | at Toronto Maple Leafs | ||
| Mar 17, 1960 | Toronto Maple Leafs | 6-2 | at Montreal Canadiens | ||
| Apr 7, 1960 | Montreal Canadiens | 4-2 | at Montreal Canadiens | Postseason | |
| Apr 9, 1960 | Montreal Canadiens | 2-1 | at Montreal Canadiens | Postseason | |
| Apr 12, 1960 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | Postseason | |
| Apr 14, 1960 | Montreal Canadiens | 4-0 | at Toronto Maple Leafs | Postseason | |
| 1958-59 (12-6-1) | Oct 16, 1958 | Montreal Canadiens | 4-3 | at Montreal Canadiens | |
| Oct 29, 1958 | Montreal Canadiens | 5-0 | at Toronto Maple Leafs | ||
| Nov 12, 1958 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| Dec 4, 1958 | Tie | 2-2 | at Montreal Canadiens | ||
| Dec 18, 1958 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Dec 31, 1958 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | ||
| Jan 8, 1959 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Jan 21, 1959 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 5, 1959 | Toronto Maple Leafs | 6-3 | at Montreal Canadiens | ||
| Feb 11, 1959 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | ||
| Feb 25, 1959 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Mar 5, 1959 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Mar 11, 1959 | Montreal Canadiens | 6-2 | at Toronto Maple Leafs | ||
| Mar 19, 1959 | Toronto Maple Leafs | 6-3 | at Montreal Canadiens | ||
| Apr 9, 1959 | Montreal Canadiens | 5-3 | at Montreal Canadiens | Postseason | |
| Apr 11, 1959 | Montreal Canadiens | 3-1 | at Montreal Canadiens | Postseason | |
| Apr 14, 1959 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | Postseason | |
| Apr 16, 1959 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | Postseason | |
| Apr 18, 1959 | Montreal Canadiens | 5-3 | at Montreal Canadiens | Postseason | |
| 1957-58 (11-2-1) | Oct 17, 1957 | Montreal Canadiens | 9-3 | at Montreal Canadiens | |
| Oct 30, 1957 | Montreal Canadiens | 6-2 | at Toronto Maple Leafs | ||
| Oct 31, 1957 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Nov 13, 1957 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Dec 4, 1957 | Tie | 0-0 | at Toronto Maple Leafs | ||
| Dec 5, 1957 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| Dec 25, 1957 | Toronto Maple Leafs | 5-4 | at Toronto Maple Leafs | ||
| Jan 2, 1958 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Jan 16, 1958 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Jan 22, 1958 | Montreal Canadiens | 2-0 | at Toronto Maple Leafs | ||
| Feb 12, 1958 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | ||
| Feb 27, 1958 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Mar 12, 1958 | Montreal Canadiens | 5-3 | at Toronto Maple Leafs | ||
| Mar 20, 1958 | Montreal Canadiens | 7-4 | at Montreal Canadiens | ||
| 1956-57 (9-4-1) | Oct 25, 1956 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | |
| Nov 7, 1956 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| Nov 29, 1956 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Dec 5, 1956 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Dec 13, 1956 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| Dec 20, 1956 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Dec 26, 1956 | Toronto Maple Leafs | 1-0 | at Toronto Maple Leafs | ||
| Jan 10, 1957 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Jan 16, 1957 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Feb 6, 1957 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Feb 14, 1957 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| Mar 6, 1957 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Mar 14, 1957 | Montreal Canadiens | 8-4 | at Montreal Canadiens | ||
| Mar 20, 1957 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| 1955-56 (9-3-2) | Oct 6, 1955 | Montreal Canadiens | 2-0 | at Montreal Canadiens | |
| Oct 26, 1955 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Nov 3, 1955 | Tie | 3-3 | at Montreal Canadiens | ||
| Nov 16, 1955 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Dec 3, 1955 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Dec 8, 1955 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Dec 28, 1955 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | ||
| Dec 29, 1955 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Jan 18, 1956 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Jan 19, 1956 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Feb 8, 1956 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Feb 16, 1956 | Montreal Canadiens | 8-1 | at Montreal Canadiens | ||
| Feb 29, 1956 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | ||
| Mar 8, 1956 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| 1954-55 (6-4-4) | Oct 21, 1954 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | |
| Oct 27, 1954 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Nov 17, 1954 | Toronto Maple Leafs | 5-2 | at Toronto Maple Leafs | ||
| Nov 18, 1954 | Montreal Canadiens | 5-4 | at Montreal Canadiens | ||
| Dec 8, 1954 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Dec 9, 1954 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Dec 29, 1954 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Jan 20, 1955 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| Jan 26, 1955 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Feb 3, 1955 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Feb 9, 1955 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 24, 1955 | Tie | 1-1 | at Montreal Canadiens | ||
| Mar 2, 1955 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Mar 10, 1955 | Tie | 0-0 | at Montreal Canadiens | ||
| 1953-54 (5-6-3) | Oct 29, 1953 | Montreal Canadiens | 3-1 | at Montreal Canadiens | |
| Nov 11, 1953 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | ||
| Nov 19, 1953 | Montreal Canadiens | 1-0 | at Montreal Canadiens | ||
| Nov 28, 1953 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Dec 3, 1953 | Montreal Canadiens | 5-1 | at Montreal Canadiens | ||
| Dec 9, 1953 | Toronto Maple Leafs | 3-0 | at Toronto Maple Leafs | ||
| Dec 30, 1953 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Jan 7, 1954 | Montreal Canadiens | 7-3 | at Montreal Canadiens | ||
| Jan 27, 1954 | Montreal Canadiens | 2-0 | at Toronto Maple Leafs | ||
| Feb 4, 1954 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Feb 13, 1954 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Feb 25, 1954 | Tie | 0-0 | at Montreal Canadiens | ||
| Mar 11, 1954 | Toronto Maple Leafs | 3-0 | at Montreal Canadiens | ||
| Mar 17, 1954 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| 1952-53 (7-5-2) | Oct 29, 1952 | Toronto Maple Leafs | 7-5 | at Toronto Maple Leafs | |
| Nov 6, 1952 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Nov 13, 1952 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Nov 22, 1952 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Dec 4, 1952 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| Dec 10, 1952 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Dec 24, 1952 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | ||
| Jan 21, 1953 | Montreal Canadiens | 1-0 | at Toronto Maple Leafs | ||
| Jan 22, 1953 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Feb 5, 1953 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Feb 14, 1953 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Feb 25, 1953 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Feb 26, 1953 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Mar 19, 1953 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | ||
| 1951-52 (8-5-1) | Oct 31, 1951 | Toronto Maple Leafs | 1-0 | at Toronto Maple Leafs | |
| Nov 1, 1951 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Nov 24, 1951 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Nov 29, 1951 | Montreal Canadiens | 5-1 | at Montreal Canadiens | ||
| Dec 20, 1951 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Dec 26, 1951 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Jan 3, 1952 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Jan 17, 1952 | Tie | 2-2 | at Montreal Canadiens | ||
| Jan 23, 1952 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Feb 9, 1952 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Feb 14, 1952 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Mar 5, 1952 | Toronto Maple Leafs | 6-2 | at Toronto Maple Leafs | ||
| Mar 13, 1952 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Mar 19, 1952 | Montreal Canadiens | 3-0 | at Toronto Maple Leafs | ||
| 1950-51 (3-14-2) | Nov 1, 1950 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | |
| Nov 2, 1950 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| Nov 16, 1950 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Nov 25, 1950 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | ||
| Nov 30, 1950 | Tie | 0-0 | at Montreal Canadiens | ||
| Dec 6, 1950 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Dec 20, 1950 | Toronto Maple Leafs | 6-1 | at Toronto Maple Leafs | ||
| Jan 18, 1951 | Toronto Maple Leafs | 5-2 | at Montreal Canadiens | ||
| Jan 24, 1951 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | ||
| Feb 1, 1951 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Feb 7, 1951 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 15, 1951 | Tie | 2-2 | at Montreal Canadiens | ||
| Mar 1, 1951 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Mar 21, 1951 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | ||
| Apr 11, 1951 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | Postseason | |
| Apr 14, 1951 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | Postseason | |
| Apr 17, 1951 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | Postseason | |
| Apr 19, 1951 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | Postseason | |
| Apr 21, 1951 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | Postseason |
1940s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1949-50 (6-4-4) | Oct 19, 1949 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | |
| Oct 27, 1949 | Toronto Maple Leafs | 2-0 | at Montreal Canadiens | ||
| Nov 10, 1949 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Nov 16, 1949 | Toronto Maple Leafs | 1-0 | at Toronto Maple Leafs | ||
| Nov 24, 1949 | Montreal Canadiens | 5-3 | at Montreal Canadiens | ||
| Dec 14, 1949 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Dec 15, 1949 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Dec 28, 1949 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Jan 18, 1950 | Montreal Canadiens | 1-0 | at Toronto Maple Leafs | ||
| Jan 19, 1950 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Feb 11, 1950 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | ||
| Feb 16, 1950 | Tie | 3-3 | at Montreal Canadiens | ||
| Mar 9, 1950 | Tie | 1-1 | at Montreal Canadiens | ||
| Mar 22, 1950 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| 1948-49 (6-4-2) | Oct 21, 1948 | Montreal Canadiens | 5-0 | at Montreal Canadiens | |
| Oct 27, 1948 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Nov 24, 1948 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Nov 25, 1948 | Toronto Maple Leafs | 2-0 | at Montreal Canadiens | ||
| Dec 30, 1948 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Jan 1, 1949 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | ||
| Jan 19, 1949 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | ||
| Feb 3, 1949 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | ||
| Feb 9, 1949 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Feb 17, 1949 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Mar 2, 1949 | Montreal Canadiens | 2-0 | at Toronto Maple Leafs | ||
| Mar 17, 1949 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| 1947-48 (6-5-1) | Oct 29, 1947 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | |
| Nov 6, 1947 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Nov 27, 1947 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Nov 29, 1947 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Dec 25, 1947 | Toronto Maple Leafs | 3-0 | at Montreal Canadiens | ||
| Jan 1, 1948 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Jan 15, 1948 | Montreal Canadiens | 8-4 | at Montreal Canadiens | ||
| Jan 28, 1948 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Feb 14, 1948 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Feb 19, 1948 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Mar 3, 1948 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Mar 11, 1948 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| 1946-47 (7-7-4) | Nov 1, 1946 | Tie | 1-1 | at Montreal Canadiens | |
| Nov 16, 1946 | Toronto Maple Leafs | 3-0 | at Toronto Maple Leafs | ||
| Dec 11, 1946 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Dec 26, 1946 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Jan 15, 1947 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Jan 16, 1947 | Tie | 1-1 | at Montreal Canadiens | ||
| Jan 30, 1947 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Feb 6, 1947 | Montreal Canadiens | 8-2 | at Montreal Canadiens | ||
| Feb 15, 1947 | Tie | 4-4 | at Toronto Maple Leafs | ||
| Feb 23, 1947 | Tie | 2-2 | at Montreal Canadiens | ||
| Feb 26, 1947 | Montreal Canadiens | 1-0 | at Toronto Maple Leafs | ||
| Mar 19, 1947 | Toronto Maple Leafs | 5-4 | at Toronto Maple Leafs | ||
| Apr 8, 1947 | Montreal Canadiens | 6-0 | at Montreal Canadiens | Postseason | |
| Apr 10, 1947 | Toronto Maple Leafs | 4-0 | at Montreal Canadiens | Postseason | |
| Apr 12, 1947 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | Postseason | |
| Apr 15, 1947 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | Postseason | |
| Apr 17, 1947 | Montreal Canadiens | 3-1 | at Montreal Canadiens | Postseason | |
| Apr 19, 1947 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | Postseason | |
| 1945-46 (7-2-1) | Nov 1, 1945 | Montreal Canadiens | 4-2 | at Montreal Canadiens | |
| Nov 14, 1945 | Montreal Canadiens | 6-1 | at Toronto Maple Leafs | ||
| Dec 8, 1945 | Montreal Canadiens | 1-0 | at Toronto Maple Leafs | ||
| Dec 13, 1945 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | ||
| Dec 26, 1945 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Jan 10, 1946 | Toronto Maple Leafs | 5-4 | at Montreal Canadiens | ||
| Feb 16, 1946 | Montreal Canadiens | 4-2 | at Toronto Maple Leafs | ||
| Feb 24, 1946 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| Mar 9, 1946 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Mar 14, 1946 | Tie | 2-2 | at Montreal Canadiens | ||
| 1944-45 (6-9-1) | Nov 2, 1944 | Toronto Maple Leafs | 4-1 | at Montreal Canadiens | |
| Nov 11, 1944 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Nov 25, 1944 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | ||
| Nov 26, 1944 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Dec 14, 1944 | Tie | 2-2 | at Montreal Canadiens | ||
| Jan 4, 1945 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Jan 11, 1945 | Montreal Canadiens | 7-4 | at Montreal Canadiens | ||
| Feb 17, 1945 | Montreal Canadiens | 4-3 | at Toronto Maple Leafs | ||
| Feb 25, 1945 | Montreal Canadiens | 5-2 | at Montreal Canadiens | ||
| Mar 3, 1945 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | ||
| Mar 20, 1945 | Toronto Maple Leafs | 1-0 | at Montreal Canadiens | Postseason | |
| Mar 22, 1945 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | Postseason | |
| Mar 24, 1945 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | Postseason | |
| Mar 27, 1945 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | Postseason | |
| Mar 29, 1945 | Montreal Canadiens | 10-3 | at Montreal Canadiens | Postseason | |
| Mar 31, 1945 | Toronto Maple Leafs | 3-2 | at Toronto Maple Leafs | Postseason | |
| 1943-44 (11-3-1) | Nov 18, 1943 | Montreal Canadiens | 5-2 | at Montreal Canadiens | |
| Nov 20, 1943 | Montreal Canadiens | 7-2 | at Toronto Maple Leafs | ||
| Dec 11, 1943 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Jan 4, 1944 | Montreal Canadiens | 6-3 | at Montreal Canadiens | ||
| Jan 11, 1944 | Toronto Maple Leafs | 5-0 | at Toronto Maple Leafs | ||
| Jan 27, 1944 | Tie | 2-2 | at Montreal Canadiens | ||
| Feb 12, 1944 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Feb 24, 1944 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Mar 4, 1944 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | ||
| Mar 5, 1944 | Montreal Canadiens | 8-3 | at Montreal Canadiens | ||
| Mar 21, 1944 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | Postseason | |
| Mar 23, 1944 | Montreal Canadiens | 5-1 | at Montreal Canadiens | Postseason | |
| Mar 25, 1944 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | Postseason | |
| Mar 28, 1944 | Montreal Canadiens | 4-1 | at Toronto Maple Leafs | Postseason | |
| Mar 30, 1944 | Montreal Canadiens | 11-0 | at Montreal Canadiens | Postseason | |
| 1942-43 (2-6-2) | Nov 21, 1942 | Toronto Maple Leafs | 8-0 | at Toronto Maple Leafs | |
| Dec 3, 1942 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Dec 5, 1942 | Toronto Maple Leafs | 9-1 | at Toronto Maple Leafs | ||
| Dec 17, 1942 | Toronto Maple Leafs | 8-1 | at Montreal Canadiens | ||
| Jan 2, 1943 | Toronto Maple Leafs | 6-3 | at Toronto Maple Leafs | ||
| Jan 3, 1943 | Tie | 4-4 | at Montreal Canadiens | ||
| Jan 16, 1943 | Toronto Maple Leafs | 8-4 | at Toronto Maple Leafs | ||
| Jan 17, 1943 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Feb 28, 1943 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Mar 6, 1943 | Tie | 2-2 | at Toronto Maple Leafs | ||
| 1941-42 (3-5) | Nov 13, 1941 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | |
| Dec 6, 1941 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Dec 11, 1941 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Jan 15, 1942 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Jan 29, 1942 | Toronto Maple Leafs | 7-3 | at Toronto Maple Leafs | ||
| Feb 12, 1942 | Toronto Maple Leafs | 6-4 | at Montreal Canadiens | ||
| Mar 5, 1942 | Montreal Canadiens | 5-2 | at Toronto Maple Leafs | ||
| Mar 19, 1942 | Montreal Canadiens | 7-3 | at Montreal Canadiens | ||
| 1940-41 (1-6-1) | Nov 14, 1940 | Toronto Maple Leafs | 6-2 | at Montreal Canadiens | |
| Nov 16, 1940 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Dec 12, 1940 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | ||
| Jan 7, 1941 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | ||
| Jan 23, 1941 | Toronto Maple Leafs | 3-2 | at Montreal Canadiens | ||
| Jan 25, 1941 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Feb 20, 1941 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Mar 6, 1941 | Montreal Canadiens | 4-3 | at Montreal Canadiens |
1930s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1939-40 (1-7) | Dec 7, 1939 | Montreal Canadiens | 4-1 | at Montreal Canadiens | |
| Dec 9, 1939 | Toronto Maple Leafs | 3-0 | at Toronto Maple Leafs | ||
| Dec 28, 1939 | Toronto Maple Leafs | 6-4 | at Montreal Canadiens | ||
| Jan 6, 1940 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Jan 27, 1940 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 17, 1940 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 18, 1940 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| Mar 14, 1940 | Toronto Maple Leafs | 8-4 | at Montreal Canadiens | ||
| 1938-39 (2-4-2) | Nov 10, 1938 | Toronto Maple Leafs | 2-0 | at Montreal Canadiens | |
| Nov 12, 1938 | Toronto Maple Leafs | 4-1 | at Toronto Maple Leafs | ||
| Dec 3, 1938 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Jan 3, 1939 | Tie | 2-2 | at Toronto Maple Leafs | ||
| Jan 12, 1939 | Toronto Maple Leafs | 9-4 | at Montreal Canadiens | ||
| Feb 11, 1939 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Feb 12, 1939 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | ||
| Mar 2, 1939 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| 1937-38 (1-4-3) | Nov 18, 1937 | Tie | 6-6 | at Montreal Canadiens | |
| Dec 4, 1937 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Dec 16, 1937 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | ||
| Jan 1, 1938 | Toronto Maple Leafs | 6-4 | at Toronto Maple Leafs | ||
| Feb 1, 1938 | Montreal Canadiens | 6-1 | at Montreal Canadiens | ||
| Feb 3, 1938 | Toronto Maple Leafs | 3-0 | at Toronto Maple Leafs | ||
| Mar 6, 1938 | Toronto Maple Leafs | 6-3 | at Montreal Canadiens | ||
| Mar 12, 1938 | Tie | 3-3 | at Toronto Maple Leafs | ||
| 1936-37 (2-6) | Nov 26, 1936 | Toronto Maple Leafs | 4-2 | at Montreal Canadiens | |
| Nov 28, 1936 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Jan 7, 1937 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Jan 9, 1937 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Jan 26, 1937 | Montreal Canadiens | 3-1 | at Toronto Maple Leafs | ||
| Feb 25, 1937 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Mar 6, 1937 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Mar 18, 1937 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| 1935-36 (2-6) | Nov 19, 1935 | Toronto Maple Leafs | 7-2 | at Montreal Canadiens | |
| Nov 30, 1935 | Toronto Maple Leafs | 8-3 | at Toronto Maple Leafs | ||
| Dec 26, 1935 | Toronto Maple Leafs | 2-0 | at Montreal Canadiens | ||
| Jan 11, 1936 | Montreal Canadiens | 7-3 | at Toronto Maple Leafs | ||
| Jan 30, 1936 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Feb 20, 1936 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Mar 7, 1936 | Toronto Maple Leafs | 8-1 | at Toronto Maple Leafs | ||
| Mar 12, 1936 | Toronto Maple Leafs | 6-3 | at Montreal Canadiens | ||
| 1934-35 (1-5) | Nov 10, 1934 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | |
| Dec 25, 1934 | Toronto Maple Leafs | 6-2 | at Montreal Canadiens | ||
| Jan 5, 1935 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Jan 17, 1935 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| Mar 5, 1935 | Toronto Maple Leafs | 10-3 | at Montreal Canadiens | ||
| Mar 16, 1935 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | ||
| 1933-34 (4-2) | Nov 25, 1933 | Montreal Canadiens | 1-0 | at Toronto Maple Leafs | |
| Dec 14, 1933 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Dec 16, 1933 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Jan 4, 1934 | Montreal Canadiens | 4-1 | at Montreal Canadiens | ||
| Feb 10, 1934 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Feb 20, 1934 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| 1932-33 (3-3) | Nov 24, 1932 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | |
| Dec 20, 1932 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| Jan 28, 1933 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | ||
| Feb 7, 1933 | Montreal Canadiens | 2-0 | at Montreal Canadiens | ||
| Feb 28, 1933 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Mar 2, 1933 | Montreal Canadiens | 4-3 | at Montreal Canadiens | ||
| 1931-32 (4-2-2) | Nov 14, 1931 | Tie | 1-1 | at Toronto Maple Leafs | |
| Nov 26, 1931 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Dec 24, 1931 | Toronto Maple Leafs | 2-1 | at Montreal Canadiens | ||
| Dec 26, 1931 | Montreal Canadiens | 2-0 | at Toronto Maple Leafs | ||
| Jan 21, 1932 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Jan 23, 1932 | Toronto Maple Leafs | 2-0 | at Toronto Maple Leafs | ||
| Mar 5, 1932 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Mar 22, 1932 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| 1930-31 (3-2-1) | Dec 9, 1930 | Montreal Canadiens | 2-1 | at Montreal Canadiens | |
| Jan 3, 1931 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Jan 10, 1931 | Montreal Canadiens | 6-1 | at Montreal Canadiens | ||
| Jan 17, 1931 | Toronto Maple Leafs | 3-1 | at Toronto Maple Leafs | ||
| Feb 3, 1931 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| Feb 28, 1931 | Tie | 5-5 | at Toronto Maple Leafs |
1920s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1929-30 (4-1-1) | Nov 21, 1929 | Montreal Canadiens | 3-2 | at Montreal Canadiens | |
| Dec 7, 1929 | Montreal Canadiens | 1-0 | at Toronto Maple Leafs | ||
| Jan 4, 1930 | Toronto Maple Leafs | 4-3 | at Toronto Maple Leafs | ||
| Feb 4, 1930 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Feb 6, 1930 | Tie | 3-3 | at Toronto Maple Leafs | ||
| Feb 27, 1930 | Montreal Canadiens | 6-2 | at Montreal Canadiens | ||
| 1928-29 (1-3-2) | Nov 17, 1928 | Toronto Maple Leafs | 4-2 | at Toronto Maple Leafs | |
| Dec 4, 1928 | Toronto Maple Leafs | 3-1 | at Montreal Canadiens | ||
| Jan 17, 1929 | Tie | 1-1 | at Toronto Maple Leafs | ||
| Jan 24, 1929 | Tie | 1-1 | at Montreal Canadiens | ||
| Feb 23, 1929 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| Mar 12, 1929 | Montreal Canadiens | 2-1 | at Montreal Canadiens | ||
| 1927-28 (3-2-1) | Dec 8, 1927 | Montreal Canadiens | 2-1 | at Montreal Canadiens | |
| Jan 7, 1928 | Montreal Canadiens | 9-1 | at Toronto Maple Leafs | ||
| Feb 2, 1928 | Toronto Maple Leafs | 4-3 | at Montreal Canadiens | ||
| Feb 7, 1928 | Montreal Canadiens | 2-1 | at Toronto Maple Leafs | ||
| Feb 21, 1928 | Tie | 0-0 | at Montreal Canadiens | ||
| Mar 17, 1928 | Toronto Maple Leafs | 5-3 | at Toronto Maple Leafs | ||
| 1926-27 (5-1) | Dec 2, 1926 | Montreal Canadiens | 2-0 | at Montreal Canadiens | |
| Dec 18, 1926 | Montreal Canadiens | 2-0 | at Toronto St. Patricks | ||
| Jan 22, 1927 | Montreal Canadiens | 4-0 | at Montreal Canadiens | ||
| Feb 24, 1927 | Montreal Canadiens | 3-2 | at Toronto Maple Leafs | ||
| Mar 10, 1927 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Mar 26, 1927 | Toronto Maple Leafs | 2-1 | at Toronto Maple Leafs | ||
| 1925-26 (3-3) | Dec 12, 1925 | Toronto St. Patricks | 4-0 | at Toronto St. Patricks | |
| Jan 5, 1926 | Montreal Canadiens | 5-4 | at Montreal Canadiens | ||
| Jan 23, 1926 | Toronto St. Patricks | 6-2 | at Toronto St. Patricks | ||
| Jan 26, 1926 | Montreal Canadiens | 6-3 | at Montreal Canadiens | ||
| Mar 11, 1926 | Toronto St. Patricks | 5-3 | at Toronto St. Patricks | ||
| Mar 16, 1926 | Montreal Canadiens | 6-1 | at Montreal Canadiens | ||
| 1924-25 (5-3) | Nov 29, 1924 | Montreal Canadiens | 7-1 | at Montreal Canadiens | |
| Dec 17, 1924 | Montreal Canadiens | 5-2 | at Toronto St. Patricks | ||
| Jan 3, 1925 | Montreal Canadiens | 3-1 | at Toronto St. Patricks | ||
| Jan 21, 1925 | Toronto St. Patricks | 4-2 | at Montreal Canadiens | ||
| Feb 7, 1925 | Toronto St. Patricks | 5-4 | at Toronto St. Patricks | ||
| Feb 25, 1925 | Toronto St. Patricks | 3-1 | at Montreal Canadiens | ||
| Mar 11, 1925 | Montreal Canadiens | 3-2 | at Montreal Canadiens | Postseason | |
| Mar 13, 1925 | Montreal Canadiens | 2-0 | at Toronto St. Patricks | Postseason | |
| 1923-24 (4-4) | Dec 15, 1923 | Toronto St. Patricks | 2-1 | at Toronto St. Patricks | |
| Dec 29, 1923 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| Jan 12, 1924 | Toronto St. Patricks | 5-3 | at Toronto St. Patricks | ||
| Jan 19, 1924 | Toronto St. Patricks | 2-0 | at Montreal Canadiens | ||
| Jan 26, 1924 | Toronto St. Patricks | 2-1 | at Toronto St. Patricks | ||
| Feb 9, 1924 | Montreal Canadiens | 5-3 | at Montreal Canadiens | ||
| Feb 27, 1924 | Montreal Canadiens | 6-1 | at Montreal Canadiens | ||
| Mar 1, 1924 | Montreal Canadiens | 4-1 | at Toronto St. Patricks | ||
| 1922-23 (4-3-1) | Dec 16, 1922 | Toronto St. Patricks | 7-2 | at Toronto St. Patricks | |
| Dec 30, 1922 | Montreal Canadiens | 8-2 | at Montreal Canadiens | ||
| Jan 13, 1923 | Tie | 2-2 | at Toronto St. Patricks | ||
| Jan 20, 1923 | Montreal Canadiens | 3-1 | at Montreal Canadiens | ||
| Jan 27, 1923 | Toronto St. Patricks | 4-2 | at Toronto St. Patricks | ||
| Feb 10, 1923 | Montreal Canadiens | 5-3 | at Montreal Canadiens | ||
| Feb 24, 1923 | Toronto St. Patricks | 4-3 | at Toronto St. Patricks | ||
| Feb 28, 1923 | Montreal Canadiens | 3-0 | at Montreal Canadiens | ||
| 1921-22 (4-4) | Dec 17, 1921 | Toronto St. Patricks | 5-2 | at Toronto St. Patricks | |
| Dec 31, 1921 | Montreal Canadiens | 5-3 | at Montreal Canadiens | ||
| Jan 21, 1922 | Toronto St. Patricks | 5-3 | at Montreal Canadiens | ||
| Jan 25, 1922 | Toronto St. Patricks | 3-1 | at Toronto St. Patricks | ||
| Feb 4, 1922 | Toronto St. Patricks | 3-1 | at Toronto St. Patricks | ||
| Feb 8, 1922 | Montreal Canadiens | 6-4 | at Montreal Canadiens | ||
| Feb 18, 1922 | Montreal Canadiens | 6-4 | at Montreal Canadiens | ||
| Mar 8, 1922 | Montreal Canadiens | 8-7 | at Toronto St. Patricks | ||
| 1920-21 (3-5) | Dec 25, 1920 | Toronto St. Patricks | 5-4 | at Toronto St. Patricks | |
| Jan 17, 1921 | Montreal Canadiens | 9-5 | at Montreal Canadiens | ||
| Jan 19, 1921 | Toronto St. Patricks | 7-2 | at Toronto St. Patricks | ||
| Jan 29, 1921 | Montreal Canadiens | 4-2 | at Montreal Canadiens | ||
| Feb 5, 1921 | Toronto St. Patricks | 10-6 | at Toronto St. Patricks | ||
| Feb 9, 1921 | Toronto St. Patricks | 5-3 | at Montreal Canadiens | ||
| Feb 28, 1921 | Montreal Canadiens | 4-0 | at Montreal Canadiens | ||
| Mar 7, 1921 | Toronto St. Patricks | 6-4 | at Toronto St. Patricks |
1910s
| Season | Date | Winner | Score | Site | Round |
|---|---|---|---|---|---|
| 1919-20 (5-3) | Dec 31, 1919 | Toronto St. Patricks | 5-1 | at Toronto St. Patricks | |
| Jan 10, 1920 | Montreal Canadiens | 14-7 | at Montreal Canadiens | ||
| Jan 14, 1920 | Montreal Canadiens | 4-3 | at Toronto St. Patricks | ||
| Jan 21, 1920 | Montreal Canadiens | 3-2 | at Montreal Canadiens | ||
| Feb 4, 1920 | Montreal Canadiens | 6-5 | at Toronto St. Patricks | ||
| Feb 18, 1920 | Toronto St. Patricks | 8-2 | at Montreal Canadiens | ||
| Mar 10, 1920 | Montreal Canadiens | 7-2 | at Montreal Canadiens | ||
| Mar 13, 1920 | Toronto St. Patricks | 11-4 | at Toronto St. Patricks | ||
| 1918-19 (6-3) | Dec 23, 1918 | Montreal Canadiens | 4-3 | at Toronto Arenas | |
| Dec 28, 1918 | Montreal Canadiens | 6-3 | at Montreal Canadiens | ||
| Jan 7, 1919 | Montreal Canadiens | 7-6 | at Toronto St. Patricks | ||
| Jan 11, 1919 | Montreal Canadiens | 13-4 | at Montreal Canadiens | ||
| Jan 21, 1919 | Toronto St. Patricks | 11-3 | at Toronto St. Patricks | ||
| Feb 1, 1919 | Montreal Canadiens | 10-0 | at Montreal Canadiens | ||
| Feb 4, 1919 | Toronto St. Patricks | 6-3 | at Toronto St. Patricks | ||
| Feb 11, 1919 | Toronto St. Patricks | 6-4 | at Toronto St. Patricks | ||
| Feb 15, 1919 | Montreal Canadiens | 8-2 | at Montreal Canadiens | ||
| 1917-18 (6-6) | Dec 26, 1917 | Toronto Arenas | 7-5 | at Toronto Arenas | |
| Dec 29, 1917 | Montreal Canadiens | 9-2 | at Montreal Canadiens | ||
| Jan 9, 1918 | Toronto Arenas | 6-4 | at Toronto Arenas | ||
| Jan 19, 1918 | Montreal Canadiens | 5-1 | at Montreal Canadiens | ||
| Jan 28, 1918 | Toronto Arenas | 5-1 | at Toronto Arenas | ||
| Feb 2, 1918 | Montreal Canadiens | 11-2 | at Montreal Canadiens | ||
| Feb 9, 1918 | Toronto Arenas | 7-3 | at Montreal Canadiens | ||
| Feb 18, 1918 | Montreal Canadiens | 9-0 | at Toronto Arenas | ||
| Feb 20, 1918 | Montreal Canadiens | 5-4 | at Montreal Canadiens | ||
| Mar 2, 1918 | Toronto Arenas | 5-3 | at Toronto Arenas | ||
| Mar 11, 1918 | Toronto Arenas | 7-3 | at Toronto Arenas | Postseason | |
| Mar 13, 1918 | Montreal Canadiens | 4-3 | at Montreal Canadiens | Postseason |