| Year | Champion Runner-up |
|
|---|---|---|
| | ||
| 2021 | Tampa Bay Lightning 4 Montreal Canadiens 1 | |
| 2020 | Tampa Bay Lightning 4 Dallas Stars 2 | |
| 2019 | St. Louis Blues 4 Boston Bruins 3 | |
| 2018 | Washington Capitals 4 Las Vegas Golden Knights 1 | |
| 2017 | Pittsburgh Penguins 4 Nashville Predators 2 | |
| 2016 | Pittsburgh Penguins 4 San Jose Sharks 2 | |
| 2015 | Chicago Blackhawks 4 Tampa Bay Lightning 2 | |
| 2014 | Los Angeles Kings 4 New York Rangers 1 | |
| 2013 | Chicago Blackhawks 4 Boston Bruins 2 | |
| 2012 | Los Angeles Kings 4 New Jersey Devils 2 | |
| 2011 | Boston Bruins 4 Vancouver Canucks 3 | |
| 2010 | Chicago Blackhawks 4 Philadelphia Flyers 2 | |
| 2009 | Pittsburgh Penguins 4 Detroit Redwings 3 | |
| 2008 | Detroit Red Wings 4 Pittsburgh Penguins 2 | |
| 2007 | Anaheim Ducks 4 Ottawa Senators 1 | |
| 2006 | Carolina Hurricanes 4 Edmonton Oilers 3 | |
| 2005 | Season cancelled due to a labor dispute. | |
| 2004 | Tampa Bay Lightning 4 Calgary Flames 3 | |
| 2003 | New Jersey Devils 4 Anaheim Mighty Ducks 3 | |
| 2002 | Detroit Red Wings 4 Carolina Hurricanes 1 | |
| 2001 | Colorado Avalanche 4 New Jersey Devils 3 | |
| 2000 | New Jersey Devils 4 Dallas Stars 2 | |
| 1999 | Dallas Stars 4 Buffalo Sabres 2 | |
| 1998 | Detroit Red Wings 4 Washington Capitals 0 | |
| 1997 | Detroit Red Wings 4 Philadelphia Flyers 0 | |
| 1996 | Colorado Avalanche 4 Florida Panthers 0 | |
| 1995 | New Jersey Devils 4 Detroit Red Wings 0 | |
| 1994 | New York Rangers 4 Vancouver Canucks 3 | |
| 1993 | Montreal Canadiens 4 Los Angeles Kings 1 | |
| 1992 | Pittsburgh Penguins 4 Chicago Blackhawks 0 | |
| 1991 | Pittsburgh Penguins 4 Minnesota North Stars 2 | |
| 1990 | Edmonton Oilers 4 Boston Bruins 1 | |
| 1989 | Calgary Flames 4 Montreal Canadiens 2 | |
| 1988 | Edmonton Oilers 4 Boston Bruins 0 | |
| 1987 | Edmonton Oilers 4 Philadelphia Flyers 3 | |
| 1986 | Montreal Canadiens 4 Calgary Flames 1 | |
| 1985 | Edmonton Oilers 4 Philadelphia Fyers 1 | |
| 1984 | Edmonton Oilers 4 New York Islanders 1 | |
| 1983 | New York Islanders 4 Edmonton Oilers 0 | |
| 1982 | New York Islanders 4 Vancouver Canucks 0 | |
| 1981 | New York Islanders 4 Minnesota North Stars 1 | |
| 1980 | New York Islanders 4 Philadelphia Flyers 2 | |
| 1979 | Montreal Canadiens 4 New York Rangers 1 | |
| 1978 | Montreal Canadiens 4 Boston Bruins 2 | |
| 1977 | Montreal Canadiens 4 Boston Bruins 0 | |
| 1976 | Montreal Canadiens 4 Philadelphia Flyers 0 | |
| 1975 | Philadelphia Flyers 4 Buffalo Sabres 2 | |
| 1974 | Philadelphia Flyers 4 Boston Bruins 2 | |
| 1973 | Montreal Canadiens 4 Chicago Blackhawks 2 | |
| 1972 | Boston Bruins 4 New York Rangers 2 | |
| 1971 | Montreal Canadiens 4 Chicago Blackhawks 3 | |
| 1970 | Boston Bruins 4 St. Louis Blues 0 | |
| 1969 | Montreal Canadiens 4 St. Louis Blues 0 | |
| 1968 | Montreal Canadiens 4 St. Louis Blues 0 | |
| 1967 | Toronto Maple Leafs 4 Montreal Canadiens 2 | |
| 1966 | Montreal Canadiens 4 Detroit Red Wings 2 | |
| 1965 | Montreal Canadiens 4 Chicago Blackhawks 3 | |
| 1964 | Toronto Maple Leafs 4 Detroit Red Wings 3 | |
| 1963 | Toronto Maple Leafs 4 Detroit Red Wings 1 | |
| 1962 | Toronto Maple Leafs 4 Chicago Blackhawks 2 | |
| 1961 | Chicago Blackhawks 4 Detroit Red Wings 2 | |
| 1960 | Montreal Canadiens 4 Toronto Maple Leafs 3 | |
| 1959 | Montreal Canadiens 4 Toronto Maple Leafs 1 | |
| 1958 | Montreal Canadiens 4 Boston Bruins 2 | |
| 1957 | Montreal Canadiens 4 Boston Bruins 1 | |
| 1956 | Montreal Canadiens 4 Detroit Red Wings 1 | |
| 1955 | Detroit Red Wings 4 Montreal Canadiens 3 | |
| 1954 | Detroit Red Wings 4 Montreal Canadiens 3 | |
| 1953 | Montreal Canadiens 4 Boston Bruins 1 | |
| 1952 | Detroit Red Wings 4 Montreal Canadiens 0 | |
| 1951 | Toronto Maple Leafs 4 Montreal Canadiens 1 | |
| 1950 | Detroit Red Wings 4 New York Rangers 3 | |
| 1949 | Toronto Maple Leafs 4 Detroit Red Wings 0 | |
| 1948 | Toronto Maple Leafs 4 Detroit Red Wings 0 | |
| 1947 | Toronto Maple Leafs 4 Montreal Canadiens 2 | |
| 1946 | Montreal Canadiens 4 Boston Bruins 1 | |
| 1945 | Toronto Maple Leafs 4 Detroit Red Wings 3 | |
| 1944 | Montreal Canadiens Chicago Blackhawks | |
| 1943 | Detroit Red Wings 4 Boston Bruins 0 | |
| 1942 | Toronto Maple Leafs 4 Detroit Red Wings 3 | |
| 1941 | Boston Bruins 4 Detroit Red Wings 0 | |
| 1940 | New York Rangers 4 Toronto Maple Leafs 2 | |
| 1939 | Boston Bruins 4 Toronto Maple Leafs 2 | |
| 1938 | Chicago Blackhawks 3 Toronto Maple Leafs 1 | |
| 1937 | Detroit Red Wings 3 New York Rangers 2 | |
| 1936 | Detroit Red Wings 3 Toronto Maple Leafs 1 | |
| 1935 | Montreal Maroons 3 Toronto Maple Leafs 0 | |
| 1934 | Chicago Blackhawks 3 Detroit Red Wings 1 | |
| 1933 | New York Rangers 3 Toronto Maple Leafs 1 | |
| 1932 | Toronto Maple Leafs 3 New York Rangers 0 | |
| 1931 | Montreal Canadiens 3 Chicago Blackhawks 2 | |
| 1930 | Montreal Canadiens 2 Boston Bruins 0 | |
| 1929 | Boston Bruins 2 New York Rangers 0 | |
| 1928 | New York Rangers 3 Montreal Maroons 2 | |
| 1927 | Ottawa Senators 2 Boston Bruins 0 | |
| 1926 | Montreal Maroons 3 Victoria Cougars 1 | |
| 1925 | Victoria Cougars 3 Montreal Canadiens 1 | |
| 1924 | Montreal Canadiens 2 Calgary Tigers 0 | |
| 1923 | Ottawa Senators 2 Edmonton Eskimos 0 | |
| 1922 | Toronto St. Pats 3 Vancouver Millionaires 2 | |
| 1921 | Ottawa Senators 3 Vancouver Millionaires 2 | |
| 1920 | Ottawa Senators 3 Seattle Metropolitans 2 | |
| 1919 | No decisions due to influenza epidemic Seattle Metropolitans Montreal | |
| 1918 | Toronto Arenas 3 Vancouver Millionaires 2 |
|
|
| 1917 | Seattle Metropolitans Montreal Canadiens |
| 1916 | Montreal Canadiens Portland Rosebuds |
| 1915 | Vancouver Millionaires Ottawa Senators |
| 1914 | Toronto Blueshirts Victoria Cougars/Montreal Canadiens |
| 1913 | Quebec Bulldogs Sydney Miners |
| 1912 | Quebec Bulldogs Moncton Victories |
| 1911 | Ottawa Senators Port Arthur Bearcats |
| 1910 | Montreal Wanderers/Ottawa Senators Berlin Union Jacks/Edmonton Eskimos |
| 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 Wheatkings/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 Malboros/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 |
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