1918--Toronto Arenas

1919--No Decision-x1920--Ottawa Senators

1921--Ottawa Senators

1922--Toronto St. Patricks

1923--Ottawa Senators

1924--Montreal Canadiens

1925--Victoria Cougars

1926--Montreal Maroons

1927--Ottawa Senators

1928--New York Rangers

1929--Boston Bruins

1930--Montreal Canadiens

1931--Montreal Canadiens

1932--Toronto Maple Leafs

1933--New York Rangers

1934--Chicago Black Hawks

1935--Montreal Maroons

1936--Detroit Red Wings

1937--Detroit Red Wings

1938--Chicago Black Hawks

1939--Boston Bruins

1940--New York Rangers

1941--Boston Bruins

1942--Toronto Maple Leafs

1943--Detroit Red Wings

1944--Montreal Canadiens

1945--Toronto Maple Leafs

1946--Montreal Canadiens

1947--Toronto Maple Leafs

1948--Toronto Maple Leafs

1949--Toronto Maple Leafs

1950--Detroit Red Wings

1951--Toronto Maple Leafs

1952--Detroit Red Wings

1953--Montreal Canadiens

1954--Detroit Red Wings

1955--Detroit Red Wings

1956--Montreal Canadiens

1957--Montreal Canadiens

1958--Montreal Canadiens

1959--Montreal Canadiens

1960--Montreal Canadiens

1961--Chicago Black Hawks

1962--Toronto Maple Leafs

1963--Toronto Maple Leafs

1964--Toronto Maple Leafs

1965--Montreal Canadiens

1966--Montreal Canadiens

1967--Toronto Maple Leafs

1968--Montreal Canadiens

1969--Montreal Canadiens

1970--Boston Bruins

1971--Montreal Canadiens

1972--Boston Bruins

1973--Montreal Canadiens

1974--Philadelphia Flyers

1975--Philadelphia Flyers

1976--Montreal Canadiens

1977--Montreal Canadiens

1978--Montreal Canadiens

1979--Montreal Canadiens

1980--New York Islanders

1981--New York Islanders

1982--New York Islanders

1983--New York Islanders

1984--Edmonton Oilers

1985--Edmonton Oilers

1986--Montreal Canadiens

1987--Edmonton Oilers

1988--Edmonton Oilers

1989--Calgary Flames

1990--Edmonton Oilers

1991--Pittsburgh Penguins

1992--Pittsburgh Penguins

1993--Montreal Canadiens

1994--New York Rangers

1995--New Jersey Devils

1996--Colorado Avalanche

1997--Detroit Red Wings

1998--Detroit Red Wings

1999--Dallas Stars

2000--New Jersey Devils

x-The series between Montreal and Seattle was called off because of an influenza epidemic.