 | Members | Stanley Cup |
| Year | Winner | Coach | Against | Coach | |
| 2002 | Carolina vs Detroit | ||||
| 2001 | Colorado Avalanche | Marc Crawford | New Jersey Devils | Jacques Lemaire | |
| 2000 | New Jersey Devils | Jacques Lemaire | Dallas Stars | Ken Hitchcock | |
| 1999 | Dallas Stars | Ken Hitchcock | Buffalo Sabres | Lindy Ruff | |
| 1998 | Detroit Red Wings | Scotty Bowman | Washington Capitals | Ron Wilson | |
| 1997 | Detroit Red Wings | Scotty Bowman | Philadelphia Flyers | Terry Murray | |
| 1996 | Colorado Avalanche | Marc Crawford | Florida Panthers | Doug MacLean | |
| 1995 | New Jersey Devils | Jacques Lemaire | Detroit Red Wings | Scotty Bowman | |
| 1994 | New York Rangers | Mike Keenan | Vancouver Canucks | Pat Quinn | |
| 1993 | Montreal Canadiens | Jacques Demers | Los Angeles Kings | Barry Melrose | |
| 1992 | Pittsburgh Penguins | Scotty Bowman | Chicago Blackhawks | Mike Keenan | |
| 1991 | Pittsburgh Penguins | Bob Johnson | Minnesota North Stars | Bob Gainey | |
| 1990 | Edmonton Oilers | John Muckler | Boston Bruins | Mike Milbury | |
| 1989 | Calgary Flames | Terry Crisp | Montreal Canadiens | Pat Burns | |
| 1988 | Edmonton Oilers | Glen Sather | Boston Bruins | Terry O'Reilly | |
| 1987 | Edmonton Oilers | Glen Sather | Philadelphia Flyers | Mike Keenan | |
| 1986 | Montreal Canadiens | Jean Perron | Calgary Flames | Bob Johnson | |
| 1985 | Edmonton Oilers | Glen Sather | Philadelphia Fyers | Mike Keenan | |
| 1984 | Edmonton Oilers | Glen Sather | New York Islanders | Al Arbour | |
| 1983 | New York Islanders | Al Arbour | Edmonton Oilers | Glen Sather | |
| 1982 | New York Islanders | Al Arbour | Vancouver Canucks | Roger Neilson | |
| 1981 | New York Islanders | Al Arbour | Minnesota North Stars | Glen Sonmor | |
| 1980 | New York Islanders | Al Arbour | Philadelphia Flyers | Pat Quinn | |
| 1979 | Montreal Canadiens | Scotty Bowman | New York Rangers | Fred Shero | |
| 1978 | Montreal Canadiens | Scotty Bowman | Boston Bruins | Don Cherry | |
| 1977 | Montreal Canadiens | Scotty Bowman | Boston Bruins | Don Cherry | |
| 1976 | Montreal Canadiens | Scotty Bowman | Philadelphia Flyers | Fred Shero | |
| 1975 | Philadelphia Flyers | Fred Shero | Buffalo Sabres | Floyd Smith | |
| 1974 | Philadelphia Flyers | Fred Shero | Boston Bruins | A Guidolin | |
| 1973 | Montreal Canadiens | Scotty Bowman | Chicago Blackhawks | William Reay | |
| 1972 | Boston Bruins | Tom Johnson | New York Rangers | Emile Francis | |
| 1971 | Montreal Canadiens | Al MacNeil | Chicago Blackhawks | Billy Reay | |
| 1970 | Boston Bruins | Harry Sinden | Saint Louis Blues | Scotty Bowman | |
| 1969 | Montreal Canadiens | Claude Ruel | Saint Louis Blues | Scotty Bowman | |
| 1968 | Montreal Canadiens | Hector Blake | Saint Louis Blues | Scotty Bowman | |
| 1967 | Toronto Maple Leafs | G Imlach | Montreal Canadiens | Hector Blake | |
| 1966 | Montreal Canadiens | Hector Blake | Detroit Red Wings | Sid Abel | |
| 1965 | Montreal Canadiens | Hector Blake | Chicago Blackhawks | Billy Reay | |
| 1964 | Toronto Maple Leafs | G Imlach | Detroit Red Wings | Sid Abel | |
| 1963 | Toronto Maple Leafs | G Imlach | Detroit Red Wings | Sid Abel | |
| 1962 | Toronto Maple Leafs | G Imlach | Chicago Blackhawks | Rudy Pilous | |
| 1961 | Chicago Blackhawks | Rudy Pilous | Detroit Red Wings | Sid Abel | |
| 1960 | Montreal Canadiens | Hector Blake | Toronto Maple Leafs | G Imlach | |
| 1959 | Montreal Canadiens | Hector Blake | Toronto Maple Leafs | G Imlach | |
| 1958 | Montreal Canadiens | Hector Blake | Boston Bruins | Milt Schmidt | |
| 1957 | Montreal Canadiens | Hector Blake | Boston Bruins | Milt Schmidt | |
| 1956 | Montreal Canadiens | Hector Blake | Detroit Red Wings | Jimmy Skinner | |
| 1955 | Detroit Red Wings | Jimmy Skinner | Montreal Canadiens | Dick Irvin | |
| 1954 | Detroit Red Wings | Tommy Ivan | Montreal Canadiens | Dick Irvin | |
| 1953 | Montreal Canadiens | Dick Irvin | Boston Bruins | Lynn Patrick | |
| 1952 | Detroit Red Wings | Tommy Ivan | Montreal Canadiens | Dick Irvin | |
| 1951 | Toronto Maple Leafs | Joe Primeau | Montreal Canadiens | Dick Irvin | |
| 1950 | Detroit Red Wings | Tommy Ivan | New York Rangers | Lynn Patrick | |
| 1949 | Toronto Maple Leafs | Clarence Day | Detroit Red Wings | Tommy Ivan | |
| 1948 | Toronto Maple Leafs | Clarence Day | Detroit Red Wings | Tommy Ivan | |
| 1947 | Toronto Maple Leafs | Clarence Day | Montreal Canadiens | Dick Irvin | |
| 1946 | Montreal Canadiens | Dick Irvin | Boston Bruins | A Clapper | |
| 1945 | Toronto Maple Leafs | Clarence Day | Detroit Red Wings | Jack Adams | |
| 1944 | Montreal Canadiens | Dick Irvin | Chicago Blackhawks | Paul Thompson | |
| 1943 | Detroit Red Wings | Jack Adams | Boston Bruins | Art Ross | |
| 1942 | Toronto Maple Leafs | Clarence Day | Detroit Red Wings | Jack Adams | |
| 1941 | Boston Bruins | R Weiland | Detroit Red Wings | Ebbie Goodfellow | |
| 1940 | New York Rangers | Frank Boucher | Toronto Maple Leafs | Dick Irvin | |
| 1939 | Boston Bruins | Art Ross | Toronto Maple Leafs | Dick Irvin | |
| 1938 | Chicago Blackhawks | Bill Stewart | Toronto Maple Leafs | Dick Irvin | |
| 1937 | Detroit Red Wings | Jack Adams | New York Rangers | Lester Patrick | |
| 1936 | Detroit Red Wings | Jack Adams | Toronto Maple Leafs | Dick Irvin | |
| 1935 | Montreal Maroons | Tommy Gorman | Toronto Maple Leafs | Dick Irvin | |
| 1934 | Chicago Blackhawks | Tommy Gorman | Detroit Red Wings | Herbie Lewis | |
| 1933 | New York Rangers | Lester Patrick | Toronto Maple Leafs | Dick Irvin | |
| 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 | |||
| 1923 | Ottawa Senators | Edmonton Eskimos | |||
| 1922 | Toronto St Pats | Vancouver Millionaires | |||
| 1921 | Ottawa Senators | Vancouver Millionaires | |||
| 1920 | Ottawa Senators | Seatle Metropolitans | |||
| 1919 | No Cup awarded due to Influenza Epidemic | ||||
| 1918 | Toronto Arenas | Vancouver Millionaires | |||
| 1917 | Seattle Metropolitans | ||||
| 1916 | Montreal Canadiens | ||||
| 1915 | Vancouver Millionaires | ||||
| 1914 | Toronto Blueshirts | ||||
| 1913 | Quebec Bulldogs | ||||
| 1912 | Quebec Bulldogs | ||||
| 1911 | Ottawa Senators | ||||
| 1910 | Montreal Wanderers Ottawa Senators | ||||
| 1909 | Ottawa Senators | ||||
| 1908 | Montreal Wanderers | ||||
| 1907 | Montreal Wanderers | ||||
| 1906 | Ottawa Silver Seven Montreal Wanderers | ||||
| 1905 | Ottawa Silver Seven | ||||
| 1904 | Ottawa Silver Seven | ||||
| 1903 | Montreal AAA Ottawa Silver Seven | ||||
| 1902 | Winnipeg Victorias Montreal AAA | ||||
| 1901 | Winnipeg Victorias | ||||
| 1900 | Montreal Shamrocks | ||||
| 1899 | Montreal Shamrocks Montreal Victorias | ||||
| 1898 | Montreal Victorias | ||||
| 1897 | Montreal Victorias | ||||
| 1896 | Montreal Victorias Winnipeg Victorias | ||||
| 1895 | Montreal Victorias | ||||
| 1894 | Montreal AAA | ||||
| 1893 | Montreal AAA | ||||
