| Award Overview | | Name | Date
| | Montreal AAA | 1893
| | Montreal AAA | 1894
| | Montreal Victorias | 1895
| | Winnepeg Victorias; February | 1896
| | Montreal Victorias; December | 1896
| | Montreal Victorias | 1897
| | Montreal Victorias | 1898
| | Montreal Shamrocks | 1899
| | Montreal Shamrocks | 1900
| | Winnepeg Victorias | 1901
| | Winnepeg Victorias | 1902
| | Montreal AAA | 1902
| | Ottawa Silver Seven | 1903
| | Ottawa Silver Seven | 1904
| | Ottawa Silver Seven | 1905
| | Montreal Wanderers | 1906
| | Kenora Thistles | 1907
| | Montreal Wanderers | 1907
| | Montreal Wanderers | 1908
| | Ottawa Senators | 1909
| | Montreal Wanderers | 1910
| | Ottawa Senators | 1911
| | Quebec Bulldogs | 1912
| | Quebec Bulldogs | 1913
| | Toronto Blueshirts | 1914
| | Vancouver Millionaires | 1915
| | Montreal Canadiens | 1916
| | Seattle Metropolitans | 1917
| | Toronto Arenas | 1918
| | Montreal-Seattle, series cancelled due to flu epidemic | 1919
| | Ottawa | 1920
| | Ottawa | 1921
| | Toronto St. Patricks | 1922
| | Ottawa | 1923
| | Montreal | 1924
| | Victoria | 1925
| | Montreal Maroons | 1926
| | Ottawa Senators | 1927
| | NY Rangers | 1928
| | Boston Bruins | 1929
| | Montreal Canadiens | 1930
| | Montreal Canadiens | 1931
| | Toronto Maple Leafs | 1932
| | New York Rangers | 1933
| | Chicago Blackhawks | 1934
| | Montreal Maroons | 1935
| | Detroit Red Wings | 1936
| | Detroit Red Wings | 1937
| | Chicago Blackhawks | 1938
| | Boston Bruins | 1939
| | New York Rangers | 1940
| | Boston Bruins | 1941
| | Toronto Maple Leafs | 1942
| | Detroit Red Wings | 1943
| | Montreal Canadiens | 1944
| | Toronto Maple Leafs | 1945
| | Montreal Canadiens | 1946
| | Toronto Maple Leafs | 1947
| | Toronto Maple Leafs | 1948
| | Toronto Maple Leafs | 1949
| | Detroit Red Wings | 1950
| | Toronto Maple Leafs | 1951
| | Detroit Red Wings | 1952
| | Montreal Canadiens | 1953
| | Detroit Red Wings | 1954
| | Detroit Red Wings | 1955
| | Montreal Canadiens | 1956
| | Montreal Canadiens | 1957
| | Montreal Canadiens | 1958
| | Montreal Canadiens | 1959
| | Montreal Canadiens | 1960
| | Chicago Blackhawks | 1961
| | Toronto Maple Leafs | 1962
| | Toronto Maple Leafs | 1963
| | Toronto Maple Leafs | 1964
| | Montreal Canadiens | 1965
| | Montreal Canadiens | 1966
| | Toronto Maple Leafs | 1967
| | Montreal Canadiens | 1968
| | Montreal Canadiens | 1969
| | Boston Bruins | 1970
| | Montreal Canadiens | 1971
| | Boston Bruins | 1972
| | Montreal Canadiens | 1973
| | Philadelphia Flyers | 1974
| | Philadelphia Flyers | 1975
| | Montreal Canadiens | 1976
| | Montreal Canadiens | 1977
| | Montreal Canadiens | 1978
| | Montreal Canadiens | 1979
| | New York Islanders | 1980
| | New York Islanders | 1981
| | New York Islanders | 1982
| | New York Islanders | 1983
| | Edmonton Oilers | 1984
| | Edmonton Oilers | 1985
| | Montreal Canadiens | 1986
| | Edmonton Oilers | 1987
| | Edmonton Oilers | 1988
| | Calgary Flames | 1989
| | Edmonton Oilers | 1990
| | Pittsburgh Penguins | 1991
| | Pittsburgh Penguins | 1992
| | Montreal Canadiens | 1993
| | New York Rangers | 1994
| | New Jersey Devils | 1995
| | Colorado Avalanche | 1996
| | Detroit Red Wings | 1997
| | Detroit Red Wings | 1998
| | Dallas Stars | 1999
| | New Jersey Devils | 2000
| | Colorado Avalanche | 2001
| | Detroit Red Wings | 2002
| | New Jersey Devils | 2003
| | Tampa Bay Lightning | 2004
| | League lockout season canceled | 2005
| | Carolina Hurricanes | 2006
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