Boys Girls
| Year | Girls | Boys |
| 2002-2003 | Boissevain | Teulon |
|
2001-2002 |
Carberry | Boissevain |
| 2000-2001 | Elton | Ste. Anne |
| 1999-2000 | Neepawa | Elton |
| 1998-1999 | Neepawa | Killarney |
| 1997-1998 | Teulon | W.C.Miller (Altona) |
| 1996-1997 | Teulon | Morden |
| 1995-1996 | Warren | Morden |
| 1994-1995 | Warren | Joseph Wolinsky |
| 1993-1994 | Warren | Joseph Wolinsky |
| 1992-1993 | Warren | Boissevain |
| 1991-1992 | Ross L. Gray (Sprague) | Boissevain |
| 1990-1991 | Garden Valley (Winkler) | Virden |
| 1989-1990 | Neelin (Brandon) | Garden Valley (Winkler) |
| 1988-1989 | St. Pauls (Elie) | Portage Collegiate |
| 1987-1988 | St. Pauls (Elie) | Edward Schreyer (Beausejour) |
| 1986-1987 | Dauphin | Gimli |
| 1985-1986 | Ross L. Gray (Sprague) | Swan Valley |
| 1984-1985 | Aurthur Meighen (Portage) | Stonewall |
| 1983-1984 | Virden | Teulon |
| 1982-1983 | Warren | Morden |
| 1981-1982 | Killarney | Westgate |
| 1980-1981 | Ross L. Gray (Sprague) | Lord Selkirk |
| 1979-1980 | Westgate | Dauphin |
| 1978-1979 | Goose Lake (Roblin) | Lord Selkirk |
| 1977-1978 | Lord Selkirk | Lord Selkirk |
| 1976-1977 | Garden Valley (Winkler) | Lord Selkirk |
| 1975-1976 | Selkirk | Dauphin |
| 1974-1975 | Selkirk | Dauphin |
| 1973-1974 | Vincent Massey (Brandon) | Vincent Massey (Brandon) |
| 1972-1973 | St. Norbert | Lord Selkirk |
| 1971-1972 | Vincent Massey (Brandon) | Neelin |
| 1970-1971 | St. Norbert | Vincent Massey (Brandon) |
| 1969-1970 | W.C.Miller (Altona) | Vincent Massey (Brandon) |
| 1968-1969 | Harrison | Vincent Massey (Brandon) |
| 1967-1968 | Tec-Voc | Morden |
| 1966-1967 | Miles MacDonell | Aurthur Meighen (Portage) |
| 1965-1966 | Tec-Voc | Vincent Massey (Brandon) |
| 1964-1965 | Hamiota | Lowe Farm |
| 1963-1964 | Carman | Low Farm |