1926 - National Soccer League (NSL) Ulster 1927 - National Soccer League (NSL) Not Played 1928 - National Soccer League (NSL) Montreal CNR 1929 - National Soccer League (NSL) Montreal CNR 1930 - National Soccer League (NSL) Toronto Scottish 1931 - National Soccer League (NSL) Toronto Scottish 1932 - National Soccer League (NSL) Toronto Ulster 1933 - National Soccer League (NSL) Toronto Ulster 1934 - National Soccer League (NSL) Toronto Ulster 1935 - National Soccer League (NSL) Frood Mines 1936 - National Soccer League (NSL) Montreal Carsteel 1937 - National Soccer League (NSL) Toronto British Consols 1938 - National Soccer League (NSL) 1939 - National Soccer League (NSL) Montreal Victorias 1940 - National Soccer League (NSL) Montreal Carsteel 1941 - National Soccer League (NSL) Montreal Carsteel 1942-46 - National Soccer League (NSL) Not played during WWII 1947 - National Soccer League (NSL) Montreal Stelco 1948 - National Soccer League (NSL) Montreal Carsteel 1949 - National Soccer League (NSL) Toronto Canadians 1950 - National Soccer League (NSL) Hamilton Westinghouse 1951 - National Soccer League (NSL) Toronto St. Andrews 1952 - National Soccer League (NSL) Toronto East End Canadians 1953 - National Soccer League (NSL) Toronto Ukraina 1955 - National Soccer League (NSL) Toronto Ukraina 1956 - National Soccer League (NSL) Polish White Eagles 1957 - National Soccer League (NSL) Toronto Italia 1958 - National Soccer League (NSL) Montreal Hungaria 1959 - National Soccer League (NSL) Montreal Cantalia 1960 - National Soccer League (NSL) Toronto Italia 1961 - National Soccer League (NSL) Toronto Roma 1962 - National Soccer League (NSL) Toronto Olympia 1963 - National Soccer League (NSL) Italian Virtus 1964 - National Soccer League (NSL) Toronto Ukraina 1965 - National Soccer League (NSL) Toronto Ukraina 1966 - National Soccer League (NSL) 1966Windsor Teutonia 1967 - National Soccer League (NSL) Hamilton Primos 1968 - National Soccer League (NSL) Sudbury Italia 1969 - National Soccer League (NSL) Toronto First Portuguese 1970 - National Soccer League (NSL) 1971 - National Soccer League (NSL) Toronto Croatia 1972 - National Soccer League (NSL) Toronto Croatia 1973 - National Soccer League (NSL) Toronto Croatia 1974 - National Soccer League (NSL) Toronto Serbian White Eagles 1975 - National Soccer League (NSL) Toronto Italia 1976 - National Soccer League (NSL) Toronto Italia 1977 - National Soccer League (NSL) Montreal Castors 1978 - National Soccer League (NSL) Montreal Castors 1979 - National Soccer League (NSL) Toronto First Portuguese 1980 - National Soccer League (NSL) Toronto Falcons 1981 - National Soccer League (NSL) Hamilton Steelers 1984 - National Soccer League (NSL) Toronto Italia 1985 - National Soccer League (NSL) London Marconi 1986 - National Soccer League (NSL) Toronto Blizzard 1987 - National Soccer League (NSL) Windsor Wheels 1988 - National Soccer League (NSL) Toronto Italia 1989 - National Soccer League (NSL) Toronto Italia 1990 - National Soccer League (NSL) Toronto First Portuguese 1991 - National Soccer League (NSL) Scarborough International 1992 - National Soccer League (NSL) Toronto Croatia 1993 - National Soccer League (NSL) Toronto Rockets 1994 - Canadian National Soccer League (CNSL) Toronto Italia 1995 - Canadian National Soccer League (CNSL) St. Catharine Wolves 1996 - Canadian National Soccer League (CNSL) Toronto Italia 1997 - Canadian National Soccer League (CNSL) 1998 - Canadian Professional Soccer League (CPCL) Toronto Olympians 1999 - Canadian Professional Soccer League (CPCL) Toronto Olympians 2000 - Canadian Professional Soccer League (CPCL) Toronto Olympians 2001 - Canadian Professional Soccer League (CPCL) St. Catharines Wolves 2002 - Canadian Professional Soccer League (CPCL) Ottawa Wizards 2003 - Canadian Professional Soccer League (CPCL) Hitmen 2004 - Canadian Professional Soccer League (CPCL) Toronto Croatia 2005 - Canadian Professional Soccer League (CPCL) Oakville Blue Devils 2006 - (CSL) Italia Shooters 2007 - Canadian Soccer League (CSL) Toronto Croatia 2008 - Canadian Soccer League (CSL) Serbian White Eagles 2009 - Canadian Soccer League (CSL) Trois-Rivieres Attak 2010 - Canadian Soccer League (CSL) Galaxy 2011 - Canadian Soccer League (CSL) Toronto Croatia 2012 - Canadian Soccer League (CSL) Toronto Croatia 2013 - Canadian Soccer League (CSL) SC Waterloo 2014 - Canadian Soccer League (CSL) York Region Shooters 2015 - Canadian Soccer League (CSL) Toronto Croatia 2016 - Canadian Soccer League (CSL) Serbian White Eagles 2017 - Canadian Soccer League (CSL) York Region Shooters 2018 – Canadian Soccer League (CSL) FC Vorkuta 2019 – Canadian Soccer League (CSL) Scarborough SC