Stanley Cup Winners
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Year | Winning Team | Losers |
| 2011 | Boston Bruins | Vancouver Canucks |
| 2010 | Chicago Black Hawks | Philadelphia Flyers |
| 2009 | Pittsburgh Penguins | Detroit Red Wings |
| 2008 | Detroit Red Wings | Pittsburgh Penguins |
| 2007 | Anaheim Ducks | Ottawa Senators |
| 2006 | Carolina Hurricanes | Edmonton Oilers |
| 2005 | Gary Betman Show | People of Canada |
| 2004 | Tampa Bay Lightning | Calgary Flames |
| 2003 | New Jersey Devils | Mighty Ducks of Anaheim |
| 2002 | Detroit Red Wings | Carolina Hurricanes |
| 2001 | Colorado Avalanche | New Jersey Devils |
| 2000 | New Jersey Devils | Dallas Stars |
| 1999 | Dallas Stars | Buffalo Sabres |
| 1998 | Detroit Red Wings | Washington Capitals |
| 1997 | Detroit Red Wings | Philadelphia Flyers |
| 1996 | Colorado Avalanche | Florida Panthers |
| 1995 | New Jersey Devils | Detroit Red Wings |
| 1994 | New York Rangers | Vancouver Canucks |
| 1993 | Montreal Canadiens | Los Angeles Kings |
| 1992 | Pittsburgh Penguins | Chicago Blackhawks |
| 1991 | Pittsburgh Penguins | Minnesota North Stars |
| 1990 | Edmonton Oilers | Boston Bruins |
| 1989 | Calgary Flames | Montreal Canadiens |
| 1988 | Edmonton Oilers | Boston Bruins |
| 1987 | Edmonton Oilers | Philadelphia Flyers |
| 1986 | Montreal Canadiens | Calgary Flames |
| 1985 | Edmonton Oilers | Philadelphia Fyers |
| 1984 | Edmonton Oilers | New York Islanders |
| 1983 | New York Islanders | Edmonton Oilers |
| 1982 | New York Islanders | Vancouver Canucks |
| 1981 | New York Islanders | Minnesota North Stars |
| 1980 | New York Islanders | Philadelphia Flyers |
| 1979 | Montreal Canadiens | New York Rangers |
| 1978 | Montreal Canadiens | Boston Bruins |
| 1977 | Montreal Canadiens | Boston Bruins |
| 1976 | Montreal Canadiens | Philadelphia Flyers |
| 1975 | Philadelphia Flyers | Buffalo Sabres |
| 1974 | Philadelphia Flyers | Boston Bruins |
| 1973 | Montreal Canadiens | Chicago Blackhawks |
| 1972 | Boston Bruins | New York Rangers |
| 1971 | Montreal Canadiens | Chicago Blackhawks |
| 1970 | Boston Bruins | St. Louis Blues |
| 1969 | Montreal Canadiens | St. Louis Blues |
| 1968 | Montreal Canadiens | St. Louis Blues |
| 1967 | Toronto Maple Leafs | Montreal Canadiens |
| 1966 | Montreal Canadiens | Detroit Red Wings |
| 1965 | Montreal Canadiens | Chicago Blackhawks |
| 1964 | Toronto Maple Leafs | Detroit Red Wings |
| 1963 | Toronto Maple Leafs | Detroit Red Wings |
| 1962 | Toronto Maple Leafs | Chicago Blackhawks |
| 1961 | Chicago Blackhawks | Detroit Red Wings |
| 1960 | Montreal Canadiens | Toronto Maple Leafs |
| 1959 | Montreal Canadiens | Toronto Maple Leafs |
| 1958 | Montreal Canadiens | Boston Bruins |
| 1957 | Montreal Canadiens | Boston Bruins |
| 1956 | Montreal Canadiens | Detroit Red Wings |
| 1955 | Detroit Red Wings | Montreal Canadiens |
| 1954 | Detroit Red Wings | Montreal Canadiens |
| 1953 | Montreal Canadiens | Boston Bruins |
| 1952 | Detroit Red Wings | Montreal Canadiens |
| 1951 | Toronto Maple Leafs | Montreal Canadiens |
| 1950 | Detroit Red Wings | New York Rangers |
| 1949 | Toronto Maple Leafs | Detroit Red Wings |
| 1948 | Toronto Maple Leafs | Detroit Red Wings |
| 1947 | Toronto Maple Leafs | Montreal Canadiens |
| 1946 | Montreal Canadiens | Boston Bruins |
| 1945 | Toronto Maple Leafs | Detroit Red Wings |
| 1944 | Montreal Canadiens | Chicago Blackhawks |
| 1943 | Detroit Red Wings | Boston Bruins |
| 1942 | Toronto Maple Leafs | Detroit Red Wings |
| 1941 | Boston Bruins | Detroit Red Wings |
| 1940 | New York Rangers | Toronto Maple Leafs |
| 1939 | Boston Bruins | Toronto Maple Leafs |
| 1938 | Chicago Blackhawks | Toronto Maple Leafs |
| 1937 | Detroit Red Wings | New York Rangers |
| 1936 | Detroit Red Wings | Toronto Maple Leafs |
| 1935 | Montreal Maroons | Toronto Maple Leafs |
| 1934 | Chicago Black Hawks | Detroit Red Wings |
| 1933 | New York Rangers | Toronto Maple Leafs |
| 1932 | Toronto Maple Leafs | New York Rangers |
| 1931 | Montreal Canadiens | Chicago Black Hawks |
| 1930 | Montreal Canadiens | Boston Bruins |
| 1929 | Boston Bruins | New York Rangers |
| 1928 | New York Rangers | Montreal Maroons |
| 1927 | Ottawa Senators | Boston Bruins |
| 1926 | Montreal Maroons | Victoria Cougars |
| 1925 | Victoria Cougars | Montreal Canadiens |
| 1924 | Montreal Canadiens | Calgary Tigers Vancouver Maroons |
| 1923 | Ottawa Senators | Edmonton Eskimos Vancouver Maroons |
| 1922 | Toronto St. Pats | Vancouver Millionaires |
| 1921 | Ottawa Senators | Vancouver Millionaires |
| 1920 | Ottawa Senators | Seattle Metropolitans |
| 1919 | No decision | |
| 1918 | Toronto Arenas | Vancouver Millionaires |
| 1917 | Seattle Metropolitans | Montreal Canadiens |
| 1916 | Montreal Canadiens | Portland Rosebuds |
| 1915 | Vancouver Millionaires | Ottawa Senators>td> |
| 1914 | Toronto Blueshirts | Victoria Cougars Montreal Canadiens |
| 1913 | Quebec Bulldogs | Sydney Miners |
| 1912 | Quebec Bulldogs | Moncton Victories |
| 1911 | Ottawa Senators | Port Arthur Bearcats Galt |
| 1910 | Montreal Wanderers Ottawa Senators | Berlin Union Jacks Edmonton Eskimos Galt |
| 1909 | Ottawa Senators | (no challengers) |
| 1908 | Montreal Wanderers | Edmonton Eskimos
Toronto Trolley Leaguers Winnipeg Maple Leafs Ottawa Victorias |
| 1907 | Montreal Wanderers Kenora Thistles | Kenora Thistles Brandon Wheat Kings Montreal Wanderers |
| 1906 | Montreal Wanderers Ottawa Silver Seven | New Glascow Cubs Ottawa Silver Seven Montreal Wanderers Smiths Falls Queen's University |
| 1905 | Ottawa Silver Seven | Rat Portage Thistles Dawson City Nuggets |
| 1904 | Ottawa Silver Seven | Brandon Wheat Kings Montreal Wanderers Toronto Marlboros Winnipeg Rowing Club |
| 1903 | Ottawa Silver Seven Montreal AAA | Rat Portage Thistles Montreal Victorias Winnipeg Victorias |
| 1902 | Montreal AAA Winnipeg Victorias | Winnipeg Victorias Toronto Wellingtons |
| 1901 | Winnipeg Victorias | Montreal Shamrocks |
| 1900 | Montreal Shamrocks | Halifax Crescents Winnipeg Victorias |
| 1899 | Montreal Shamrocks Montreal Victorias | Queen's University Winnipeg Victorias |
| 1898 | Montreal Victorias | (no challengers) |
| 1897 | Montreal Victorias | Ottawa Capitals |
| 1896 | Montreal Victorias Winnipeg Victorias | Winnipeg Victorias Montreal Victorias |
| 1895 | Montreal Victorias | (no challengers) |
| 1894 | Montreal AAA | Ottawa Generals |
| 1893 | Montreal AAA | (no challengers) |