On March 18, 1892, a player from the Ottawa Rebels delivered a message from Lord Stanley, the Earl of Preston and Governor General of Canada, to the Ottawa Amateur Athletic Association suggesting that a championship hockey game be held each year. From 1893 on, the Stanley Cup has been held every year except 1919 and 2005. The winners are as follows:
| Year | Winning Team | MVP |
|---|---|---|
| 2009 | Pittsburgh Penguins | Eugeni Malkin |
| 2008 | Detroit Red Wings | Henrik Zetterberg |
| 2007 | Anaheim Ducks | Scott Niedermayer |
| 2006 | Carolina Hurricanes | Cam Ward |
| 2005 | N/A | N/A |
| 2004 | Tampa Bay Lightning | Brad Richards |
| 2003 | New Jersey Devils | Jean-Sebastien Giguere |
| 2002 | Detroit Red Wings | Nicklas Lidstrom |
| 2001 | Colorado Avalanche | Patrick Roy |
| 2000 | New Jersey Devils | Scott Stevens |
| 1999 | Dallas Stars | Joe Nieuwendyk |
| 1998 | Detroit Red Wings | Steve Yzerman |
| 1997 | Detroit Red Wings | Mike Vernon |
| 1996 | Colorado Avalanche | Joe Sakic |
| 1995 | New Jersey Devils | Claude Lemieux |
| 1994 | New York Rangers | Brian Leetch |
| 1993 | Montreal Canadiens | Patrick Roy |
| 1992 | Pittsburgh Penguins | Mario Lemieux |
| 1991 | Pittsburgh Penguins | Mario Lemieux |
| 1990 | Edmonton Oilers | Bill Ranford |
| 1989 | Calgary Flames | Al MacInnis |
| 1988 | Edmonton Oilers | Wayne Gretzky |
| 1987 | Edmonton Oilers | Ron Hextall |
| 1986 | Montreal Canadiens | Patrick Roy |
| 1985 | Edmonton Oilers | Wayne Gretzky |
| 1984 | Edmonton Oilers | Mark Messier |
| 1983 | New York Islanders | Billy Smith |
| 1982 | New York Islanders | Mike Bossy |
| 1981 | New York Islanders | Butch Goring |
| 1980 | New York Islanders | Bryan Trottier |
| 1979 | Montreal Canadiens | Bob Gainey |
| 1978 | Montreal Canadiens | Larry Robinson |
| 1977 | Montreal Canadiens | Guy Lafleur |
| 1976 | Montreal Canadiens | Reg Leach |
| 1975 | Philadelphia Flyers | Bernie Parent |
| 1974 | Philadelphia Flyers | Bernie Parent |
| 1973 | Montreal Canadiens | Yvan Cournoyer |
| 1972 | Boston Bruins | Bobby Orr |
| 1971 | Montreal Canadiens | Ken Dryden |
| 1970 | Boston Bruins | Bobby Orr |
| 1969 | Montreal Canadiens | Serge Savard |
| 1968 | Montreal Canadiens | Glenn Hall |
| 1967 | Toronto Maple Leafs | Dave Keon |
| 1966 | Montreal Canadiens | Roger Crozier |
| 1965 | Montreal Canadiens | Jean Beliveau |
| 1964 | Toronto Maple Leafs | N/A |
| 1963 | Toronto Maple Leafs | N/A |
| 1962 | Toronto Maple Leafs | N/A |
| 1961 | Chicago Blackhawks | N/A |
| 1960 | Montreal Canadiens | N/A |
| 1959 | Montreal Canadiens | N/A |
| 1958 | Montreal Canadiens | N/A |
| 1957 | Montreal Canadiens | N/A |
| 1956 | Montreal Canadiens | N/A |
| 1955 | Detroit Red Wings | N/A |
| 1954 | Detroit Red Wings | N/A |
| 1953 | Montreal Canadiens | N/A |
| 1952 | Detroit Red Wings | N/A |
| 1951 | Toronto Maple Leafs | N/A |
| 1950 | Detroit Red Wings | N/A |
| 1949 | Toronto Maple Leafs | N/A |
| 1948 | Toronto Maple Leafs | N/A |
| 1947 | Toronto Maple Leafs | N/A |
| 1946 | Montreal Canadiens | N/A |
| 1945 | Toronto Maple Leafs | N/A |
| 1944 | Montreal Canadiens | N/A |
| 1943 | Detroit Red Wings | N/A |
| 1942 | Toronto Maple Leafs | N/A |
| 1941 | Boston Bruins | N/A |
| 1940 | New York Rangers | N/A |
| 1939 | Boston Bruins | N/A |
| 1938 | Chicago Blackhawks | N/A |
| 1937 | Detroit Red Wings | N/A |
| 1936 | Detroit Red Wings | N/A |
| 1935 | Montreal Maroons | N/A |
| 1934 | Chicago Blackhawks | N/A |
| 1933 | New York Rangers | N/A |
| 1932 | Toronto Maple Leafs | N/A |
| 1931 | Montreal Canadiens | N/A |
| 1930 | Montreal Canadiens | N/A |
| 1929 | Boston Bruins | N/A |
| 1928 | New York Rangers | N/A |
| 1927 | Ottawa Senators | N/A |
| 1926 | Montreal Maroons | N/A |
| 1925 | Victoria Cougars | N/A |
| 1924 | Montreal Canadiens | N/A |
| 1923 | Ottawa Senators | N/A |
| 1922 | Toronto St. Pats | N/A |
| 1921 | Ottawa Senators | N/A |
| 1920 | Ottawa Senators | N/A |
| 1919 | N/A | N/A |
| 1918 | Toronto Arenas | N/A |
| 1917 | Seattle Metropolitans | N/A |
| 1916 | Montreal Canadiens | N/A |
| 1915 | Vancouver Millionaires | N/A |
| 1914 | Toronto Blueshirts | N/A |
| 1913 | Quebec Bulldogs | N/A |
| 1912 | Quebec Bulldogs | N/A |
| 1911 | Ottawa Senators | N/A |
| 1910 | Montreal Wanderers, Ottawa Senators | N/A |
| 1909 | Ottawa Senators | N/A |
| 1908 | Montreal Wanderers | N/A |
| 1907 | Montreal Wanderers, Kenora Thistles | N/A |
| 1906 | Montreal Wanderers, Ottawa Silver Seven | N/A |
| 1905 | Ottawa Silver Seven | N/A |
| 1904 | Ottawa Silver Seven | N/A |
| 1903 | Ottawa Silver Seven, Montreal AAA | N/A |
| 1902 | Montreal AAA, Winnipeg Victorias | N/A |
| 1901 | Winnipeg Victorias | N/A |
| 1900 | Montreal Shamrocks | N/A |
| 1899 | Montreal Shamrocks, Montreal Victorias | N/A |
| 1898 | Montreal Victorias | N/A |
| 1897 | Montreal Victorias | N/A |
| 1896 | Montreal Victorias | N/A |
| 1895 | Montreal Victorias | N/A |
| 1894 | Montreal AAA | N/A |
| 1893 | Montreal AAA | N/A |
