| 2010's | 2000s | 1990's | 1980's | 1970's | 1960's | 1950's | 1940's | 1930's | 1920's | 1919-earlier | ||
1919 NHL FINAL |
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| Feb. 22 | Ottawa 4 | at Montreal 8 |
| Feb. 27 | Montreal 5 | at Ottawa 3 |
| 1-Mar | Ottawa 3 | at Montreal 6 |
| 3-Mar | Montreal 3 | at Ottawa 6 |
| 6-Mar | Ottawa 2 | at Montreal 4 |
| Montreal won best-of-seven series, 4-1 | ||
| 1919 PCHA FINAL | ||
| 12-Mar | Vancouver 1 | at Seattle 6 |
| 13-Mar | Seattle 1 | at Vancouver 4 |
| Seattle won total-goals series, 7-5 | ||
| 1919 STANLEY CUP FINAL | ||
| 19-Mar | Montreal 0 | at Seattle 7 |
| 22-Mar | Montreal 4 | at Seattle 2 |
| 24-Mar | Montreal 2 | at Seattle 7 |
| 26-Mar | Montreal 0 | at Seattle 0 (OT) |
| 30-Mar | Montreal 4 | at Seattle 3 (OT) |
| Series cancelled due to influenza epidemic | ||
| 1918 NHL FINAL | ||
| 11-Mar | Montreal 3 | at Toronto 7 |
| 13-Mar | Toronto 3 | at Montreal 4 |
| Toronto won total-goals series, 10-7 | ||
| 1918 PCHA FINAL | ||
| 11-Mar | Seattle 2 | at Vancouver 2 |
| 13-Mar | Vancouver 1 | at Seattle 0 |
| Vancouver won total-goals series, 3-2 | ||
| 1918 STANLEY CUP FINAL | ||
| 20-Mar | Vancouver 3 | at Toronto 5 |
| 23-Mar | Vancouver 6 | at Toronto 4 |
| 26-Mar | Vancouver 3 | at Toronto 6 |
| 28-Mar | Vancouver 8 | at Toronto 1 |
| 30-Mar | Vancouver 1 | at Toronto 2 |
| Toronto won best-of-five series, 3-2 | ||
| 1917 NHA PLAYOFF | ||
| 7-Mar | Ottawa 2 | at Montreal 5 |
| 10-Mar | Montreal 2 | at Ottawa 4 |
| Montreal won total-goals series, 7-6 | ||
| 1917 STANLEY CUP FINAL | ||
| 17-Mar | Montreal 8 | at Seattle 4 |
| 20-Mar | Montreal 1 | at Seattle 6 |
| 23-Mar | Montreal 1 | at Seattle 4 |
| 26-Mar | Montreal 1 | at Seattle 9 |
| Seattle won best-of-five series, 3-1 | ||
| 1916 STANLEY CUP FINAL | ||
| 20-Mar | Portland 2 | at Montreal 0 |
| 22-Mar | Portland 1 | at Montreal 2 |
| 25-Mar | Portland 3 | at Montreal 6 |
| 28-Mar | Portland 6 | at Montreal 5 |
| 30-Mar | Portland 1 | at Montreal 2 |
| Montreal won best-of-five series, 3-2 | ||
| 1915 NHA PLAYOFF | ||
| 10-Mar | Mtl. Wanderers 0 | at Ottawa 4 |
| 13-Mar | Ottawa 0 | at Mtl. Wanderers 1 |
| Ottawa won total-goals series, 4-1 | ||
| 1915 STANLEY CUP FINAL | ||
| 22-Mar | Ottawa 2 | at Vancouver 6 |
| 24-Mar | Ottawa 3 | at Vancouver 8 |
| 26-Mar | Ottawa 3 | at Vancouver 12 |
| Vancouver won best-of-five series, 3-0 | ||
| 1914 NHA PLAYOFF | ||
| 7-Mar | Toronto 0 | at Montreal 2 |
| 11-Mar | Montreal 0 | at Toronto 6 |
| Toronto won total-goals series, 6-2 | ||
| 1914 STANLEY CUP FINAL | ||
| 14-Mar | Victoria 2 | at Toronto 5 |
| 17-Mar | Victoria 5 | at Toronto 6 (OT) |
| 19-Mar | Victoria 1 | at Toronto 2 |
| Toronto won best-of-five series, 3-0 | ||
| 1913 CUP CHALLENGE | ||
| 8-Mar | Sydney 3 | at Quebec 14 |
| 10-Mar | Sydney 2 | at Quebec 6 |
| Quebec won best-of-three series, 2-0 | ||
| 1912 CHALLENGE SEMI-FINAL | ||
| 2-Mar | Saskatoon 1 | vs Port Arthur 11 |
| 4-Mar | Saskatoon 5 | at Port Arthur 1 |
| Port Arthur won total-goals series, 12-6. Chose not to challenge NHA champions. |
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| 1912 CUP CHALLENGE | ||
| 11-Mar | Moncton 3 | at Quebec 9 |
| 13-Mar | Moncton 0 | at Quebec 8 |
| Quebec won best-of-three series, 2-0 | ||
| 1911 OPHL PLAYOFF | ||
| 1-Mar | Galt 8 | vs Waterloo 0 |
| Galt won one-game series | ||
| 1911 CHALLENGE SEMI-FINALS | ||
| 3-Mar | Port Hope 4 | at Galt 8 |
| 7-Mar | Galt 4 | at Port Hope 4 |
| Galt won total-goals series, 12-8 | ||
| 8-Mar | Port Arthur 6 | vs Prince Albert 3 |
| 10-Mar | Port Arthur 6 | vs Prince Albert 5 |
| Port Arthur won total goals series, 12-8 | ||
| 1911 CUP CHALLENGES | ||
| 13-Mar | Galt 4 | at Ottawa 7 |
| Ottawa won one-game challenge | ||
| 16-Mar | Port Arthur 4 | at Ottawa 14 |
| Ottawa won one-game challenge | ||
| 1910 March CUP CHALLENGE | ||
| 12-Mar | Berlin 3 | at Mtl. Wanderers 7 |
| Montreal won one-game challenge | ||
| 1910 January CUP CHALLENGES | ||
| Jan. 5 | Galt 3 | at Ottawa 12 |
| Jan. 7 | Galt 1 | at Ottawa 3 |
| Ottawa won total-goals series, 15-4 | ||
| Jan. 18 | Edmonton 4 | at Ottawa 8 |
| Jan. 20 | Edmonton 7 | at Ottawa 13 |
| Ottawa won total-goals series, 21-11 | ||
| 1909 OPHL PLAYOFF | ||
| Feb. 25 | Brantford 1 | at Galt 7 |
| Galt won one-game tiebreaker | ||
| 1908 December CUP CHALLENGE | ||
| Dec. 28 | Edmonton 3 | at Mtl. Wanderers 7 |
| Dec. 30 | Edmonton 7 | at Mtl. Wanderers 6 |
| Montreal won total-goals series, 13-10 | ||
| 1908 March CUP CHALLENGES | ||
| 10-Mar | Winnipeg 5 | at Mtl. Wanderers 11 |
| 12-Mar | Winnipeg 3 | at Mtl. Wanderers 9 |
| Montreal won total-goals series, 20-8 | ||
| 14-Mar | Toronto 4 | at Mtl. Wanderers 6 |
| Montreal won one-game challenge 1-0 | ||
| 1908 January CHALLENGE SEMI-FINAL | ||
| Dec. 27 | Renfrew 1 | at Ottawa 4 |
| Dec. 30 | Ottawa 1 | at Renfrew 3 |
| Ottawa won total-goals series, 5-4 | ||
| 1908 CUP CHALLENGE | ||
| Jan. 9 | Ottawa 3 | at Mtl. Wanderers 9 |
| Jan. 13 | Ottawa 1 | at Mtl. Wanderers 13 |
| Montreal won total-goals series, 22-4 | ||
| 1907 March CUP PLAYOFF | ||
| 16-Mar | Kenora 8 | vs Brandon 6 |
| 18-Mar | Kenora 4 | vs Brandon 1 |
| Kenora won best-of-three series, 2-0 | ||
| 1907 CUP CHALLENGE | ||
| 23-Mar | Mtl. Wanderers 7 | vs Kenora 2 |
| 25-Mar | Mtl. Wanderers 5 | vs Kenora 6 |
| Montreal won total-goals series, 12-8. | ||
| 1907 January CUP CHALLENGE | ||
| Jan. 17 | Kenora 4 | at Mtl. Wanderers 2 |
| Jan. 21 | Kenora 8 | at Mtl. Wanderers 6 |
| Kenora won best-of-three series, 2-0 | ||
| 1906 December CUP CHALLENGE | ||
| Dec. 27 | New Glasgow 3 | at Mtl. Wanderers 10 |
| Dec. 29 | New Glasgow 2 | at Mtl. Wanderers 7 |
| Montreal won total-goals series, 17-5 | ||
| 1906 March CUP CHALLENGE | ||
| 6-Mar | Smiths Falls 5 | at Ottawa 6 |
| 8-Mar | Smiths Falls 2 | at Ottawa 8 |
| Ottawa won total-goals series, 14-7 | ||
| 1906 NOVA SCOTIA PLAYOFF | ||
| 6-Mar | New Glasgow 7 | at Halifax Wanderers 1 |
| New Glasgow won one-game tiebreaker | ||
| 1906 MARITIME PLAYOFF | ||
| 12-Mar | Moncton 1 | at New Glasgow 7 |
| 14-Mar | Moncton 1 | at New Glasgow 2 (OT) (OT) |
| New Glasgow won best-of-three series, 2-0 | ||
| 1906 MANITOBA PLAYOFF | ||
| 8-Mar | Kenora 5 | at Winnipegs 2 |
| Kenora won one-game tiebreaker | ||
| 1906 CUP PLAYOFF | ||
| 14-Mar | Ottawa 1 | at Mtl. Wanderers 9 |
| 17-Mar | Mtl. Wanderers 3 | at Ottawa 9 |
| Montreal won total-goals series, 12-10 | ||
| 1906 February CUP CHALLENGE | ||
| Feb. 27 | Queen's U. 7 | at Ottawa 16 |
| Feb. 28 | Queen's U. 7 | at Ottawa 12 |
| Ottawa won total-goals series, 28-14 | ||
| 1905 March CUP CHALLENGE | ||
| 7-Mar | Rat Portage 9 | at Ottawa 3 |
| 9-Mar | Rat Portage 2 | at Ottawa 4 |
| 11-Mar | Rat Portage 4 | at Ottawa 5 |
| Ottawa won best-of-three series, 2-1 | ||
| 1905 January CUP CHALLENGE | ||
| Jan. 13 | Dawson City 2 | at Ottawa 9 |
| Jan. 16 | Dawson City 2 | at Ottawa 23 |
| Ottawa won best-of-three series, 2-0 | ||
| 1904 March CUP CHALLENGES | ||
| 2-Mar | Ottawa 5 | at Mtl. Wanderers 5 |
| Series awarded to Ottawa | ||
| 9-Mar | Brandon 3 | at Ottawa 6 |
| 11-Mar | Brandon 3 | at Ottawa 9 |
| Ottawa won total-goals series, 15-6 | ||
| 1904 February CUP CHALLENGE | ||
| Feb. 23 | Tor. Marlboros 3 | at Ottawa 6 |
| Feb. 25 | Tor. Marlboros 2 | at Ottawa 11 |
| Ottawa won best-of-three series, 2-0 | ||
| 1904 January CUP CHALLENGE | ||
| Dec. 30 | Winnipeg R.C. 1 | at Ottawa 9 |
| Jan. 1 | Winnipeg R.C. 6 | at Ottawa 2 |
| Jan. 4 | Winnipeg R.C. 0 | at Ottawa 2 |
| Ottawa won best-of-three series, 2-1 | ||
| 1903 March CUP PLAYOFF | ||
| 7-Mar | Ottawa 1 | at Mtl. Victorias 1 |
| 10-Mar | Mtl. Victorias 0 | at Ottawa 8 |
| Ottawa won total-goals series, 9-1 | ||
| 1903 CUP CHALLENGE | ||
| 12-Mar | Rat Portage 2 | at Ottawa 6 |
| 14-Mar | Rat Portage 2 | at Ottawa 4 |
| Ottawa won total-goals series, 10-4 | ||
| 1903 February CUP CHALLENGE | ||
| Jan. 29 | Winnipeg 1 | at Mtl. AAA 8 |
| Jan. 31 | Winnipeg 2 | at Mtl. AAA 2 (OT) |
| Feb. 2 | Winnipeg 4 | at Mtl. AAA 2 |
| Feb. 4 | Winnipeg 1 | at Mtl. AAA 4 |
| Montreal won best-of-three series, 2-1 | ||
| 1902 March CUP CHALLENGE | ||
| 13-Mar | Mtl. AAA 0 | at Winnipeg 1 |
| 15-Mar | Mtl. AAA 5 | at Winnipeg 0 |
| 17-Mar | Mtl. AAA 2 | at Winnipeg 1 |
| Montreal won best-of-three series, 2-1 | ||
| 1902 January CUP CHALLENGE | ||
| Jan. 21 | Tor. Wellingtons 3 | at Winnipeg 5 |
| Jan. 23 | Tor. Wellingtons 3 | at Winnipeg 5 |
| Winnipeg won best-of-three series, 2-0 | ||
| 1901 CUP CHALLENGE | ||
| Jan. 29 | Winnipeg 4 | at Mtl. Shamrocks 3 |
| Jan. 31 | Winnipeg 2 | at Mtl. Shamrocks 1 (OT) |
| Winnipeg won best-of-three series, 2-0 | ||
| 1900 March CUP CHALLENGE | ||
| 5-Mar | Halifax 2 | at Mtl. Shamrocks 10 |
| 7-Mar | Halifax 0 | at Mtl. Shamrocks 11 |
| Montreal won total-goals series, 21-2 | ||
| 1900 February CUP CHALLENGE | ||
| Feb. 12 | Winnipeg 4 | at Mtl. Shamrocks 3 |
| Feb. 14 | Winnipeg 2 | at Mtl. Shamrocks 3 |
| Feb. 16 | Winnipeg 4 | at Mtl. Shamrocks 5 |
| Montreal won best-of-three series, 2-1 | ||
| 1899 March CUP CHALLENGE | ||
| 14-Mar | Queen's U. 2 | at Mtl. Shamrocks 6 |
| Montreal won one-game challenge | ||
| 1899 February CUP CHALLENGE | ||
| Feb. 15 | Winnipeg 1 | at Mtl. Victorias 2 |
| Feb. 18 | Winnipeg 2 | at Mtl. Victorias 3 |
| Montreal won best-of-three series, 2-0 | ||
| 1898 | ||
| No Cup Challenge games played in 1898 | ||
| 1897 CUP CHALLENGE | ||
| Dec. 27 | Ottawa 2 | at Mtl. Victorias 14 |
| Montreal declared series, winner | ||
| 1896 December CUP CHALLENGE | ||
| Dec. 30 | Mtl. Victorias 6 | at Winnipeg 5 |
| Montreal won one-game challenge | ||
| 1896 February CUP CHALLENGE | ||
| Feb. 14 | Winnipeg 2 | at Mtl. Victorias 0 |
| Winnipeg won one-game challenge | ||
| 1895 CUP CHALLENGE | ||
| 9-Mar | Queen's U. 1 | at Mtl. AAA 5 |
| Montreal won one-game challenge | ||
| 1894 SEMIFINAL | ||
| 17-Mar | Mtl. Victorias 2 | at Mtl. AAA 3 |
| 1894 FINAL | ||
| 22-Mar | Ottawa 1 | at Mtl. AAA 3 |
| 1893 | ||
| Cup awarded to Montreal AAA after schedule concluded |
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