| Season | NSL Playoff Champions | NSL Playoff Finalists |
| 1926 | Ulster United | Montreal Maroons |
| 1927 | Not completed | |
| 1928 | Montreal C.N.R. | Ulster United |
| 1929 | Montreal C.N.R. | Ulster United |
| 1930 | Toronto Scottish | Montreal C.N.R. |
| 1931 | Toronto Scottish | Montreal Carsteel |
| 1932 | Ulster United | Montreal Carsteel |
| 1933 | Ulster United | Montreal Carsteel |
| 1934 | Ulster United | Montreal Carsteel |
| 1935 | Frood Mines | Ulster United |
| 1936 | Montreal Carsteel | Ulster United |
| 1937 | British Consols | Falconbridge Falcons |
| 1938 | Royal Victoria Hospital | Ulster United |
| 1939 | Royal Victoria Hospital | British Consols |
| 1940 | Montreal Carsteel | Toronto Maple Leafs |
| 1941 | Ulster United | Montreal Carsteel |
| Season | NSL (Montreal) Champions | OMSL Champions |
| 1942 | Montreal Carsteel | |
| 1943 | Montreal Vickers | |
| 1944 | ||
| 1945 | Montreal Carsteel | |
| 1946 | Ulster United | |
| Season | NSL Playoff Champions | NSL League Champions |
| 1947 | Montreal Stelco | |
| Season | NSL Playoff Champions | NSL Playoff Finalists |
| 1948 | Montreal Carsteel | Hamilton Westinghouse |
| 1949 | East End Canadians | Montreal Carsteel |
| 1950 | Hamilton Westinghouse | Montreal Canadian Falcons |
| Season | NSL Playoff Champions | NSL League Champions |
| 1951 | Toronto Ukraina | Toronto St. Andrews |
| 1952 | East End Canadians | |
| 1953 | Toronto Ukraina | Toronto Ukraina |
| 1954 | Ulster United | Toronto Ukraina |
| 1955 | Ulster United | Toronto Ukraina |
| 1956 | Polish White Eagles | Polish White Eagles |
| 1957 | Toronto Italia | Toronto Italia |
| 1958 | Montreal Hungaria | Montreal Hungaria |
| 1959 | Toronto Italia | Montreal Cantalia |
| 1960 | Toronto Italia | Toronto Italia |
| 1961 | Toronto Ukraina | Toronto Roma |
| 1962 | Italian Virtus | Olympia-Harmonie |
| 1963 | Toronto Ukraina | Italian Virtus |
| 1964 | Toronto Ukraina | Toronto Ukraina |
| 1965 | Toronto Hakoah | Toronto Ukraina |
| 1966 | Windsor Teutonia | Sudbury Italia |
| 1967 | Windsor Teutonia | Hamilton Primos |
| 1968 | Sudbury Italia | Sudbury Italia |
| 1969 | First Portuguese | |
| 1970 | Hamilton Croatia | Toronto Croatia |
| 1971 | Toronto Croatia | Toronto Croatia |
| 1972 | Toronto Italia | Toronto Croatia |
| 1973 | Toronto Hungaria | Toronto Croatia |
| 1974 | Toronto Croatia | Serbian White Eagles |
| 1975 | Toronto Italia | |
| 1976 | First Portuguese | Toronto Italia |
| 1977 | Montreal Castors | |
| 1978 | Toronto Falcons | Montreal Castors |
| 1979 | First Portuguese | |
| 1980 | Panhellenic Olympics | Toronto Falcons |
| 1981 | Hamilton Steelers | Hamilton Steelers |
| 1982 | Hamilton Steelers | Toronto Italia |
| 1983 | Panhellenic | |
| 1984 | Toronto Italia | Toronto Italia |
| 1985 | Toronto Italia | London Marconi |
| 1986 | Toronto Italia | Toronto Blizzard |
| 1987 | Toronto Italia | Windsor Wheels |
| 1988 | Toronto Croatia | Toronto Italia |
| 1989 | Toronto Italia | |
| 1990 | First Portuguese | |
| 1991 | Toronto Italia | |
| 1992 | Toronto Croatia | |
| 1993 | St. Catharines Roma | Toronto Rockets |
| 1994 | Toronto Italia | Toronto Italia |
| 1995 | St. Catharines Wolves | St. Catharines Wolves |
| 1996 | Toronto Italia | Toronto Italia |
| 1997 | St. Catharines Wolves | St. Catharines Wolves |
Seasons:
National Soccer League 