Championship Games: LOSSA
| 2007 | Donald A. Wilson | 20 | Paul Dwyer | 16 | |
| 2006 | Pickering | 38 | Donald A. Wilson | 0 | |
| 2005 | Pickering | 28 | Paul Dwyer | 4 | |
| 2004 | Pickering | 30 | St. Mary | 13 | |
| 2003 | St. Mary | 27 | Paul Dwyer | 18 | |
| 2002 | St. Mary | 21 | Dunbarton | 14 | |
| 2001 | St. Mary | 41 | Henry Street | 12 | |
| 2000 | Nov. 11th | St. Mary | 15 | Pickering | 7 |
| 1999 | St. Mary | 29 | Pickering | 10 | |
| 1998 |
League did not operate: Labour dispute |
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| 1997 | Henry Street | 41 | Pine Ridge | 14 | |
| 1996 | Uxbridge | 14 | Dunbarton | 0 | |
| 1995 | Dunbarton | 24 | Pickeirng | 23 | |
| 1994 | Pickering | 32 | Dunbarton | 9 | |
| 1993 | Pickering | 40 | Paul Dwyer | 0 | |
| 1992 | Paul Dwyer | 7 | Pickering | 6 | |
| 1991 | Henry Street | 14 | Pickering | 12 | |
| 1990 | Pickering | 42 | Dr. F. J. Donevan | 12 | |
| 1989 | Pickering | 17 | Dr. F. J. Donevan | 14 | |
| 1988 | Pickering | 23 | Paul Dwyer | 21 | |
| 1987 | Paul Dwyer | 7 | O'Neill | 0 | |
| 1986 | Pickering | 22 | Dr. F. J. Donevan | 15 | |
| 1985 | Henry Street | 1 | Pickering | 0 | |
| 1984 | Paul Dwyer | 21 | Dr. F. J. Donevan | 0 | |
| 1983 | Pickering | 27 | Henry Street | 6 | |
| 1982 | Paul Dwyer | 35 | Dr. F. J. Donevan | 8 | |
| 1981 | Pickering | 21 | Paul Dwyer | 19 | |
| 1980 | Henry Street | 35 | McLaughlin | 6 | |
| 1979 | Henry Street | 22 | Uxbridge | 13 | |
| 1978 | Paul Dwyer | 34 | Henry Street | 14 | |
| 1977 | Henry Street | 17 | Pickering | 6 | |
| 1976 | Pickering |
7 |
Eastdale | 0 | |
| 1975 | Pickering | 41 | Anderson | 0 | |
| 1974 | Eastdale | 6 | Anderson | 0 | |
| 1973 | Oshawa Catholic | 37 | Port Perry | 6 | |
| 1972 |
Labour dispute |
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| 1971 | Oshawa Central Collegiate | 18 | Eastdale | 0 | |
Senior B
2004: Paul Dwyer 10, Eastdale 3
Lake Ontario COSSA Senior
1951/11/10: Peterborough 24, Oshawa 0
1950: Peterborough
1949: Peterborough
1948: Peterborough
1947: Peterborough
1946: Peterborough
1945: Peterborough
COSSA Group Junior
1946/11/09 Lindsay 12, Bowmanville 9 (advance from group to play Bowmanville for
district honours)