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| Toronto Italia FC | 11 |
| (1957, 1960, 1975, 1976, 1985, 1986, 1987, 1988, 1989, 1994, 1996) | | Toronto Croatia CNSC | 9 |
| (1970, 1971, 1972, 1973, 2000, 2004, 2007, 2011, 2012) | | Toronto Ulster FC | 7 |
| (1922, 1923, 1924, 1926, 1932, 1933, 1934) | | Toronto Ukrainians FC | 5 |
| (1953, 1954, 1955, 1964, 1965) | | St. Catharines Roma SC | 4 |
| (1993, 1995, 1997, 2001) | | Montrèal Carsteel FC | 4 |
| (1936, 1940, 1941, 1948) | | Toronto Olympians FC | 3 |
| (1962, 1998, 1999) | | Toronto First Portuguese FC | 3 |
| (1969, 1979, 1990) | | Serbian White Eagles FC | 2 |
| (1974, 2008) | | Montrèal Castors FC | 2 |
| (1977, 1978) | | Montrèal Victorians FC | 2 |
| (1938, 1939) | | Toronto Scottish FC | 2 |
| (1930, 1931) | | Montrèal NCR | 2 |
| (1928, 1929) | | Waterloo SC | 1 |
| (2013) | | Brantford Galaxy FC | 1 |
| (2010) | | Trois-Rivières Attak FC | 1 |
| (2009) | | Italia Shooters FC | 1 |
| (2006) | | Brampton City United FC | 1 |
| (2005) | | Brampton Hitmen FC | 1 |
| (2003) | | Ottawa Wizards FC | 1 |
| (2002) | | Woodbridge Azzurri FC | 1 |
| (1992) | | Scarborough International FC | 1 |
| (1991) | | Dynamo Latino FC | 1 |
| (1984) | | Hamilton Steelers FC | 1 |
| (1981) | | Toronto Falcons FC | 1 |
| (1980) | | Sudbury Italia FC | 1 |
| (1968) | | Hamilton Primos FC | 1 |
| (1967) | | Windsor Teutonia FC | 1 |
| (1966) | | Italian Virtus FC | 1 |
| (1963) | | Toronto Roma FC | 1 |
| (1959) | | Montrèal Hungaria FC | 1 |
| (1958) | | Montrèal Cantalia FC | 1 |
| (1959) | | Polish White Eagles FC | 1 |
| (1956) | | Toronto East End Canadians FC | 1 |
| (1952) | | Toronto St. Andrews FC | 1 |
| (1951) | | Hamilton Westinghouse FC | 1 |
| (1950) | | Toronto Canadians FC | 1 |
| (1949) | | Montrèal Stelco FC | 1 |
| (1947) | | Toronto British Consols FC | 1 |
| (1937) | | Frood Mines FC | 1 |
| (1935) |
| Toronto FC | 4 |
| (2009, 2010, 2011, 2012) | | Impact FC Montrèal | 3 |
| (2008, 2013, 2014) |
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