Championship Games: Windsor
| 2008 | Nov. 14th | Herman | 8 | General Amherst | 7 | |
| 2007 | Nov. 9th | Holy Names | Catholic Central | |||
| 2006 | Nov. 20th | Villanova | 38 | Sandwich | 21 | |
| 2005 | Nov. 18th | Sandwich | 18 | Herman | 17 | |
| 2004 | Nov. 8th | Herman | 24 | General Amherst | 14 | |
| 2003 | Nov. 27th | Holy Names | 21 | Sandwich | 7 | |
| 2002 | Nov. 12th | Sandwich | 32 | Holy Names | 12 | |
| 2001 | Herman | 17 | Holy Names | 7 | ||
| 2000 | Nov. 22nd | Herman | 18 | Sandwich | 12 | |
| 1999 | Herman | 21 | Sandwich | 14 | ||
| 1998 | Season Cancelled | |||||
| 1997 | Riverside | 32 | Herman | 23 | ||
| 1996 | Nov. 21st | Herman | 41 | Belle River | 7 | |
| 1995 | Nov. 24th | Belle River | 21 | Holy Names | 1 | |
| 1994 | Herman | 17 | Holy Names | 13 | ||
| 1993 | Nov. 24th | Herman | 17 | Massey | 14 | Overtime |
| 1992 | Nov. 27th | Massey | 13 | Brennan | 6 | |
| 1991 | Nov. 23rd | Herman | 14 | Kennedy | 0 | |
| 1990 | Nov. 24th | Herman | 14 | Kennedy | 0 | |
| 1989 | Herman | 29 | Brennan | 7 | ||
| 1988 | Nov. 26th | Herman | 19 | Massey | 18 | Triple overtime |
| 1987 | Nov. 21st | Massey | 12 | Herman | 4 | |
| 1986 | Massey | 16 | St. Anne's | 1 | ||
| 1985 | Assumption | Herman | ||||
| 1984 | Centennial | Kennedy | ||||
| 1983 | Centennial | Assumption | ||||
| 1982 | Massey | Brennan | ||||
| 1981 | Lowe | Centennial | ||||
1978 Herman
1966 Leamington
1965 Walkerville
1955 Assumption 35, Patterson 11(Windsor Secondary Schools Association)
1948 Assumption
1986 - Tier System introduced
Senior Wilson Conference Tier II
2007 General Amherst 24, Essex 7
2006/11/20 Belle River 23, Brennan 9
2005/11/25 Cardinal Carter 25, Belle River 7
2004/11/22 Holy Names 16, St. Anne 3
2003/11/20 General Amherst 19, Massey 9
2002/11/29 Essex 16, Kennedy 13
2001/11/23 Riverside 13, Kennedy 8
2000/11/24 General Amherst 47, Massey 28
1999/11/26 Catholic Central 43, Leamington 0
1998 Season cancelled
1996/11/21 Riverside 45, Massey 10
1995/11/24 Essex 13, Riverside 9
1994/11/26 Belle River 34, Forster 9
1993/11/27 Belle River 14, Villanova 7
1992/11/27 Riverside 16, Essex 10
1991/11/22 Riverside 22, Catholic Central 8
1990/11/23 Forster 6, Catholic Central 4
1989/11/24 Forster 45, Sandwich 8
1988/11/25 Lowe 28, Walkerville 10
1987 Sandwich 21, Riverside 16
1986 Lowe won
Arnott Conference
2004/11/22 Catholic Central 24, Cardinal Carter 1
1996/11/15 Assumption 20, Cardinal Carter 10
1994 Conference did not operate
1992/11/26 General Amherst 30, Belle River 0
1991/11/21 Villanova 27, Walkerville 20
1990/11/22 General Amherst 21, Kingsville 0
1989/11/23 Catholic Central 14, Holy Names 7
1988/11/18 Essex 41, Kingsville 6
Conference launched in 1988
Junior
Janisse Division
2007/11/21 Herman 26, Villanova 0
2005/11/24 Herman 27, Holy Names 7
2004/11/24 Catholic Central 19, Herman 13
2003/11/19 Herman 33, Holy Names 17
Miller Division
2007/11/20 Cardinal Carter 21, Catholic Central 7
2005/11/22 Brennan 35, Kennedy 14
2004/11/24 Massey 24, Brennan 8
2003 General Amherst
Junior
2000/11/29 Holy Names 14, General Amherst 0
1999/12/01 Sandwich 28, Herman 6 (ECSSA vs WSSAA)
Junior: Essex County Secondary School Association
1999/11/23 Sandwich 37, General Amherst 6
199611/17 Sandwich 8, Belle River 6
1995/11/19 Belle River 14, Essex 1 (Essex County SSA)
1994 Belle River (Essex County SSA)
1993/11/14 Belle River 31, General Amherst 8 (Essex County SSA)
1992/11/22 General Amherst 21, Belle River 8 (Essex County SSA)
1991/11/17 Sandwich 27, St. Anne 7 (Essex County SSA)
1990/11/17 Sandwich defeated General Amherst (Essex County SSA)
1989/11/16 Essex 19, General Amherst 7 (Essex County SSA)
1988/11/27 General Amherst 14, St. Annes (Essex County SSA)
1988/11/27 Belle River 21, Sandwich 6 (Essex County SSA - 3rd place game)
1987 St. Annes defeated Kingsville (Essex County SSA)
1986 St. Annes 13, Sandwich 7 (Essex County SSA)
1985 St.. Annes
Junior: Windsor Secondary Schools Athletic Association
1999/11/24 Herman 26, Catholic Central 11 (City final)
1996/11/20 Herman 27, Riverside 8
1995/11/15 Brennan 10, Herman 7 (Overtime)
1994 Massey 6, Brennan 2
1993/11/17 Massey 13, Holy Names 7
1992/11/18 Herman 19, Holy Names 7
1991/11/20 Massey 23, Catholic Central 0
1990/11/21 Brennan 49, Herman 6
1989/11/22 Brennan 44, Massey 6
1988/11/16 Brennan 17, Herman 6
1987/11/11 Brennan 10, Herman 7
1986/11/19 Assumption 15, Brennan 13
1973 Massey
Essex County Secondary School Association
3rd Place Game
Sandwich 8, L'Essor 0
WOSSA
1935Windsor Vocational 63, Stratford 6 (two game total point)
1935/11/16 Windsor Vocational 25, Stratford 6
1935/11/20 Windsor Vocational 38, Stratford 0
1957 Essex County Four Conference comprised of Riverside, Essex, Leamington
and Corpus Christi
1957 Champions: Riverside, who went on to defeat London Mitchell 40-0 to win
WOSSA Senior B title