Men's Ontario Cup Champions
| Under 21 Men |
|---|
| 2004 - Ottawa St. Anthony's |
| 2005 - Mississauga Erin Mills |
| 2006 - Mississauga Erin Mills Eagles |
| 2007 - Woodbridge Strikers |
| 2008 - St. Catharines Concord Gunners |
| 2009 - Oakville SC |
| 2010 - Woodbridge Strikers |
| 2011 - Ajax Admirals |
| 2012 - Kleinburg Nobleton Red Lions |
| 2013 - Scarborough GS Power |
| 2014 - Vaughan Azzurri |
| 2015 - Vaughan Azzurri |
| 2016 - Vaughan Azzurri |
| 2017 - Vaughan Azzurri |
| 2018 - Vaughan Azzurri |
| 2019 - Vaughan Azzurri |
| 2020 - No Competition due to Covid-19 Pandemic |
| 2021 - No Competition |
| 2022 - Kleinburg Nobleton SC |
| 2023 - Klienburg Nobleton SC |
| Men |
|---|
| 1901 - Galt Football Club |
| 1902 - Galt Football Club |
| 1903 - Galt Football Club |
| 1904 - Toronto Scots |
| 1905 - Seaforth Hurons |
| 1906 - Toronto Thistles |
| 1907 - Toronto Thistles |
| 1908 - Little York |
| 1909 - Toronto Thistles |
| 1910 - Galt Football Club |
| 1911 - Hamilton Westinghouse |
| 1912 - Hamilton Westinghouse |
| 1913 - Hamilton Lancashire |
| 1914 - Toronto Eatonias |
| 1915 - Toronto Lanchshire |
| 1916 - Toronto Eastonia & |
| Hamilton Westinghouse |
| 1918 - Toronto Scottish |
| 1919 - Toronto Old Country |
| 1920 - Hamilton Westinghouse |
| 1921 - Toronto Scottish |
| 1922 - Toronto Scottish |
| 1923 - Guelph Taylor-Forbes |
| 1924 - Brantford Cockshutts |
| 1925 - Hamilton Westinghouse |
| 1926 - Toronto Willys-Overland |
| 1927 - Toronto Ulster United |
| 1928 - Toronto Scottish |
| 1929 - Toronto Ulster United |
| 1930 - Hamilton Thistles |
| 1931 - Toronto Scottish |
| 1932 - Falconbridge |
| 1933 - Falconbridge |
| 1934 - Falconbridge |
| 1935 - Toronto British Consols |
| 1936 - Toronto British Consols |
| 1937 - Toronto Ulster United |
| 1939 - Hamilton City |
| 1940 - Toronto England United |
| 1949 - Hamilton Westinghouse |
| 1941 - 1955 - No Competition |
| 1956 - Toronto Thistle |
| 1957 - Windsor Corinthians |
| 1958 - Sudbury United |
| 1959 - Hamilton City |
| 1960 - Golden Mile Football Club |
| 1961 - Windsor Caboto |
| 1962 - Toronto Royals |
| 1963 - Scarborough Thistle |
| 1964 - Sudbury Italia |
| 1965 - Oshawa Italia |
| 1966 - Italia - London Marconi |
| 1967 - Ballymena |
| 1968 - Toronto Royals |
| 1969 - Sudbury Polish White Eagles |
| 1970 - Italo Canadian Hamilton |
| 1971 - Windsor Maple Leaf Serbian |
| 1972 - San Fili |
| 1973 - Toronto West Indies United |
| 1974 - Windsor Italia |
| 1975 - Brantford Falcons |
| 1976 - Croatian Nationals |
| 1977 - Toronto Emerald |
| 1978 - London Italia Marconi |
| 1979 - Toronto Termitana |
| 1980 - Toronto Ciociaro |
| 1981 - Kitchener Waterloo Olympics |
| 1982 - Hamilton Serbians |
| 1983 - Windsor Croatia |
| 1984 - Dundas United |
| 1985 - Toronto Emerald |
| 1986 - Hamilton Steelers |
| 1987 - Scarborough Azzurri |
| 1988 - Toronto SC Braga Arsenal |
| 1989 - Scarborough Azzurri |
| 1990 - Windsor Caboto |
| 1991 - Scarborough Azzurri |
| 1992 - Scarborough Ulster Thistle |
| 1993 - Woodbridge Sora Lazio |
| 1994 - Scarborough Azzurri |
| 1995 - Windsor Croatia |
| 1996 - Scarborough Azzurri |
| 1997 - Dundas United |
| 1998 - Hamilton Serbians |
| 1999 - Woodbridge Sora Strikers |
| 2000 - Woodbridge Azzurri |
| 2001 - Aurora Hearts |
| 2002 - London Portuguese |
| 2003 - Kanata Soccer Post |
| 2004 - Ottawa Royals |
| 2005 - Scarborough GS United |
| 2006 - Ottawa St. Anthony's Premier |
| 2007 - Woodbridge Italia |
| 2008 - AEK London |
| 2009 - Real Toronto |
| 2010 - AEK London |
| 2011 - Toronto Celtic |
| 2012 - AEK London FC |
| 2013 - Gloucester Celtic |
| 2014 - London Marconi |
| 2015 - London Marconi |
| 2016 - Ottawa Gloucester Celtic |
| 2017 - Durham Celtic |
| 2018 - Caledon FC |
| 2019- Ottawa St. Anthony MP |
| 2020 - No Competition due to Covid-19 Pandemic |
| 2021 - Gloucester Celtic |
| 2022 - Gloucester Celtic |
| 2023 - West Ottawa Warriors MP |
