| Season | Stanley Cup Champion |
| 1998-1999 | Dallas Stars |
| 1997-1998 | Detrot Red Wings |
| 1996-1997 | Detrot Red Wings |
| 1995-1996 | Colorado Avalanche |
| 1994-1995 | New Jersey Devils |
| 1993-1994 | New York Rangers |
| 1992-1993 | Montreal Canadiens |
| 1991-1992 | Pittsburgh Penguins |
| 1990-1991 | Pittsburgh Penguins |
| 1989-1990 | Edmonton Oilers |
| 1988-1989 | Calgary Flames |
| 1987-1988 | Edmonton Oilers |
| 1986-1987 | Edmonton Oilers |
| 1985-1986 | Montreal Canadiens |
| 1984-1985 | Edmonton Oilers |
| 1983-1984 | Edmonton Oilers |
| 1982-1983 | New York Islanders |
| 1981-1982 | New York Islanders |
| 1980-1981 | New York Islanders |
| 1979-1980 | New York Islanders |
| 1978-1979 | Montreal Canadiens |
| 1977-1978 | Montreal Canadiens |
| 1976-1977 | Montreal Canadiens |
| 1975-1976 | Montreal Canadiens |
| 1974-1975 | Philadelphia Flyers |
| 1973-1974 | Philadelphia Flyers |
| 1972-1973 | Montreal Canadiens |
| 1971-1972 | Boston Bruins |
| 1970-1971 | Montreal Canadiens |
| 1969-1970 | Boston Bruins |
| 1968-1969 | Montreal Canadiens |
| 1967-1968 | Montreal Canadiens |
| 1966-1967 | Toronto Maple Leafs |
| 1965-1966 | Montreal Canadiens |
| 1964-1965 | Montreal Canadiens |
| 1963-1964 | Toronto Maple Leafs |
| 1962-1963 | Toronto Maple Leafs |
| 1961-1962 | Toronto Maple Leafs |
| 1960-1961 | Chicago Black Hawks |
| 1959-1960 | Montreal Canadiens |
| 1958-1959 | Montreal Canadiens |
| 1957-1958 | Montreal Canadiens |
| 1956-1957 | Montreal Canadiens |
| 1955-1956 | Montreal Canadiens |
| 1954-1955 | Detrot Red Wings |
| 1953-1954 | Detrot Red Wings |
| 1952-1953 | Montreal Canadiens |
| 1951-1952 | Detrot Red Wings |
| 1950-1951 | Toronto Maple Leafs |
| 1949-1950 | Detrot Red Wings |
| 1948-1949 | Toronto Maple Leafs |
| 1947-1948 | Toronto Maple Leafs |
| 1946-1947 | Toronto Maple Leafs |
| 1945-1946 | Montreal Canadiens |
| 1944-1945 | Toronto Maple Leafs |
| 1943-1944 | Montreal Canadiens |
| 1942-1943 | Detrot Red Wings |
| 1941-1942 | Toronto Maple Leafs |
| 1940-1941 | Boston Bruins |
| 1939-1940 | New York Rangers |
| 1938-1939 | Boston Bruins |
| 1937-1938 | Chicago Black Hawks |
| 1936-1937 | Detrot Red Wings |
| 1935-1936 | Detrot Red Wings |
| 1934-1935 | Montreal Maroons |
| 1933-1934 | Chicago Black Hawks |
| 1932-1933 | New York Rangers |
| 1931-1932 | Toronto Maple Leafs |
| 1930-1931 | Montreal Canadiens |
| 1929-1930 | Montreal Canadiens |
| 1928-1929 | Boston Bruins |
| 1927-1928 | New York Rangers |
| 1926-1927 | Ottawa Senators |
| 1925-1926 | Montreal Maroons |
| 1924-1925 | Victoria Cougars |
| 1923-1924 | Montreal Canadiens |
| 1922-1923 | Ottawa Senators |
| 1921-1922 | Toronto St. Patricks |
| 1920-1921 | Ottawa Senators |
| 1919-1920 | Ottawa Senators |
| 1918-1919 | Cup Not Awarded |
| 1917-1918 | Toronto Arenas |