| Years Held | Team | League | Method of Winning | Challengers Defeated | % Correct |
|---|---|---|---|---|---|
| 1916 | Montreal Canadiens | National Hockey Association | Series | Portland Rosebuds | 100%
|
| 1924 | Montreal Canadiens | National Hockey League | Series | Calgary Tigers | 100%
|
| 1926 | Montreal Maroons | National Hockey League | Series | Victoria Cougars | 100%
|
| 1909-1910 | Ottawa Senators | Eastern Canada Hockey Association | League | Galt Hockey ClubEdmonton Hockey Club | 100%
|
| 1911-1912 | Ottawa Senators | National Hockey Association | League | Galt Hockey ClubPort Arthur Bearcats | 100%
|
| 1920 | Ottawa Senators | National Hockey League | Series | Seattle Metropolitans | 100%
|
| 1921 | Ottawa Senators | National Hockey League | Series | Vancouver Millionaires | 100%
|
| 1923 | Ottawa Senators | National Hockey League | Series | Edmonton Eskimos | 100%
|
| 1903-1906 | Ottawa Silver Seven | Canadian Amateur Hockey League / Federal Amateur Hockey League | League | Montreal VictoriasRat Portage Thistles Winnipeg Rowing Club Toronto Marlboros Montreal Wanderers Brandon Wheat City Dawson City Nuggets Rat Portage Thistles Queen's University Smiths Falls Hockey Club | 100%
|
| 1918 | Toronto Arenas | National Hockey League | Series | Vancouver Millionaires | 100%
|
| 1922 | Toronto St. Patricks | National Hockey League | Series | Vancouver Millionaires | 100%
|
| 1915 | Vancouver Millionaires | Pacific Coast Hockey Association | Series | Ottawa Senators | 100%
|
| 1906-1907 | Montreal Wanderers | Eastern Canada Amateur Hockey Association | League | New Glasgow Cubs | 80%
|
| 1907-1909 | Montreal Wanderers | Eastern Canada Amateur Hockey Association | Challenge | Ottawa VictoriasWinnipeg Maple Leafs Toronto Pros Edmonton Hockey Club | 80%
|
| 1910-1911 | Montreal Wanderers | National Hockey Association | League | Berlin Dutchmen | 80%
|
| 1917 | Seattle Metropolitans | Pacific Coast Hockey Association | Series | Montreal Canadiens | 80%
|
| 1925 | Victoria Cougars | Western Canada Hockey League | Series | Montreal Canadiens | 80%
|
| 1912-1914 | Quebec Bulldogs | National Hockey Association | League | Moncton VictoriasSydney Millionaires | 60%
|
| 1914 | Toronto Blueshirts | National Hockey Association | League | Montreal CanadiensVictoria Aristocrats | 60%
|
| 1907 | Kenora Thistles | Manitoba Professional Hockey League | Challenge | Brandon Wheat City | 40%
|
| 1893-1895 | Montreal Hockey Club | Amateur Hockey Association of Canada | League | Ottawa Hockey ClubQueen's University | 40%
|
| 1899-1901 | Montreal Shamrocks | Canadian Amateur Hockey League | League | Queen's University Winnipeg Victorias Halifax Crescents | 40%
|
| 1895-1896 | Montreal Victorias | Amateur Hockey Association of Canada | League | 40%
| |
| 1896-1899 | Montreal Victorias | Amateur Hockey Association of Canada / Canadian Amateur Hockey League | Challenge | Ottawa CapitalsWinnipeg Victorias | 40%
|
| 1896 | Winnipeg Victorias | Manitoba Hockey Association | Challenge | 40%
| |
| 1901-1902 | Winnipeg Victorias | Manitoba Hockey Association | Challenge | Winnipeg Hockey Club Toronto Wellingtons | 40%
|
| 1902-1903 | Montreal Hockey Club | Canadian Amateur Hockey League | Challenge | Winnipeg Victorias | 20%
|