National Soccer League (NSL)
1926: Toronto Ulster
1927: Not Played
1928: Montreal CNR
1929: Montreal CNR
1930: Toronto Scottish
1931: Toronto Scottish
1932: Toronto Ulster
1933: Toronto Ulster
1934: Toronto Ulster
1935: Frood Mines
1936: Montreal Carsteel
1937: Toronto British Consols
1938: Montreal Victorias
1939: Montreal Victorias
1940: Montreal Carsteel
1941: Montreal Carsteel
1942-46: Not played during WWII
1947: Montreal Stelco
1948: Montreal Carsteel
1949: Toronto Canadians
1950: Hamilton Westinghouse
1951: Toronto St. Andrews
1952: Toronto East End Canadians
1953: Toronto Ukraina
1954: Toronto Ukraina
1955: Toronto Ukraina
1956: Polish White Eagles
1957: Toronto Italia
1958: Montreal Hungaria
1959: Montreal Cantalia
1960: Toronto Italia
1961: Toronto Roma
1962: Toronto Olympia
1963: Italian Virtus
1964: Toronto Ukraina
1965: Toronto Ukraina
1966: Windsor Teutonia
1967: Hamilton Primos
1968: Sudbury Italia
1969: Toronto First Portuguese
1970: Toronto Croatia
1971: Toronto Croatia
1972: Toronto Croatia
1973: Toronto Croatia
1974: Toronto Serbian White Eagles
1975: Toronto Italia
1976: Toronto Italia
1977: Montreal Castors
1978: Montreal Castors
1979: Toronto First Portuguese
1980: Toronto Falcons
1981: Hamilton Steelers
1984: Toronto Italia
1985: London Marconi
1986: Toronto Blizzard
1987: Windsor Wheels
1988: Toronto Italia
1989: Toronto Italia
1990: Toronto First Portuguese
1991: Scarborough International
1992: Toronto Croatia
1993: Toronto Rockets