| Year | Champion |
|---|---|
| 1963-1964 | Junior Boys - Donevan |
| 1964-1965 | Junior Boys - Donevan |
| 1965-1966 | Junior Boys - Donevan |
| 1966-1967 | Junior Boys - Donevan |
| 1967-1968 | Junior Boys - |
| 1968-1969 | Junior Boys - |
| 1969-1970 | Junior Boys - O\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\'Neill |
| 1970-1971 | Junior Boys - Anderson |
| 1971-1972 | Junior Boys - |
| 1972-1973 | Midget Boys - Anderson Junior Boys - |
| 1973-1974 | Midget Boys - Junior Boys - Anderson |
| 1974-1975 | Midget Boys - Henry Street Junior Boys - |
| 1975-1976 | Midget Boys - Henry Street Junior Boys - Pickering |
| 1976-1977 | Midget Boys - Henry Street Junior Boys - Pickering |
| 1977-1978 | Midget Boys - Junior Boys - Anderson |
| 1978-1979 | Midget Boys - Henry Street Junior Boys - Dunbarton |
| 1979-1980 | Midget Boys - Henry Street Junior Boys - Anderson |
| 1980-1981 | Midget Boys - Junior Boys - Henry |
| 1981-1982 | Midget Boys - Junior Boys - Dunbarton |
| 1982-1983 | Midget Boys - Dunbarton Junior Boys - Anderson |
| 1983-1984 | Midget Boys - Dunbarton Junior Boys - Anderson |
| 1984-1985 | Midget Boys - Dunbarton Junior Boys - Dunbarton |
| 1985-1986 | Midget Boys - Dunbarton Junior Boys - Anderson |
| 1986-1987 | Midget Boys - Anderson Junior Boys - Brock |
| 1987-1988 | Midget Boys - Dunbarton Junior Boys - Dunbarton |
| 1988-1989 | Midget Boys - Bowmanville Junior Boys - Pickering |
| 1989-1990 | Midget Boys - Port Perry Junior Boys - |
| 1990-1991 | Midget Boys - Pickeirng Junior Boys - Port Perry |
| 1991-1992 | Midget Boys - Dunbarton Junior Boys - Port Perry |
| 1992-1993 | Midget Boys - Pickering Junior Boys - Pickering |
| 1993-1994 | Senior Boys - Dunbarton Midget Boys - Anderson Junior Boys - Henry Street |
| 1994-1995 | Senior Boys - Dunbarton Midget Boys - Sinclair Junior Boys - Dunbarton |
| 1995-1996 | Senior Boys - Dunbarton Midget Boys - Port Perry Junior Boys - Sinclair |
| 1996-1997 | Senior Boys - Dunbarton Midget Boys - Port Perry Junior Boys - Port Perry |
| 1997-1998 | Senior Boys - Dunbarton Midget Boys - Port Perry Junior Boys - Pickering |
| 1998-1999 | Senior Boys - Dunbarton Midget Boys - Junior Boys - |
| 1999-2000 | Senior Boys - Dunbarton Midget Boys - Port Perry Junior Boys - Dunbarton |
| 2000-2001 | Senior Boys - Dunbarton Midget Boys - Port Perry Junior Boys - Sinclair |
| 2001-2002 | Senior Boys - Dunbarton Midget Boys - Port Perry Junior Boys - Eastdale |
| 2002-2003 | Senior Boys - Uxbridge Midget Boys - Port Perry Junior Boys - Eastdale |
| 2003-2004 | Senior Boys - Uxbridge Midget Boys - O\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\'Neill Junior Boys - Uxbridge |
| 2004-2005 | Senior Boys - Uxbridge Midget Boys - Sinclair Junior Boys - |
| 2005-2006 | Senior Boys - Port Perry Midget Boys - Port Perry Junior Boys - Sinclair |
| 2006-2007 | Senior Boys - Uxbridge Midget Boys - Pine Ridge Junior Boys - Port Perry H.S. |
| 2007-2008 | Senior Boys - Eastdale Midget Boys - Uxbridge Junior Boys - Pine Ridge |
| 2008-2009 | Senior Boys - Uxbridge Midget Boys - Uxbridge Junior Boys - Uxbridge |
| 2009-2010 | Senior Boys - Uxbridge Midget Boys - Maxwell Heights Junior Boys - Dunbarton |
| 2010-2011 | Tier 2 Junior Boys - Maxwell Heights S.S. Senior Boys - Uxbridge Midget Boys - Sinclair Junior Boys - Maxwell Heights |
| 2011-2012 | Tier 2 Senior Boys - Anderson C. & V.I. Tier 2 Junior Boys - Henry St. Senior Boys - Uxbridge S.S. Midget Boys - Port Perry H.S. Junior Boys - Uxbridge S.S. |
| 2012-2013 | Tier 2 Senior Boys - Austin Senior Boys - Uxbridge Midget Boys - Uxbridge Junior Boys - Uxbridge Tier 2 Junior Boys--Richardson |
| 2013-2014 | |
| 2014-2015 | |
| 2015-2016 | Tier II Junior--St.Mary Midget--Brooklin HS Junior--Uxbridge SS Senior--Uxbridge SS |
| 2016-2017 |
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