| 2025/2026 | Softball | | Varsity | Girls | | |
| 2024/2025 | Softball | | Varsity | Girls | St-Joachim/Réal-Bérard (Co-Op) |  |
| 2023/2024 | Softball | | Varsity | Girls | Institut collégial Vincent Massey Collegiate Trojans | -c_40x40.png) |
| 2022/2023 | Softball | | Varsity | Girls | Institut collégial Vincent Massey Collegiate Trojans | |
| 2021/2022 | Softball | | Varsity | Girls | Boissevain School Broncos |  |
| 2018/2019 | Softball | | Varsity | Girls | Collège Jeanne-Sauvé Olympiens |  |
| 2017/2018 | Softball | | | Girls | Collège Stonewall Collegiate Rams |  |
| 2016/2017 | Softball | | | Girls | Portage Collegiate Institute Saints |  |
| 2015/2016 | Softball | | | Girls | Portage Collegiate Institute Saints | |
| 2014/2015 | Softball | | | Girls | Portage Collegiate Institute Saints | |
| 2013/2014 | Softball | | | Girls | Neepawa Area Collegiate Tigers |  |
| 2012/2013 | Softball | | | Girls | Nellie McClung Collegiate Stingers |  |
| 2011/2012 | Softball | | | Girls | Nellie McClung Collegiate Stingers | |
| 2009/2010 | Softball | | | Girls | W.C. Miller Collegiate Aces | -c_40x36.png) |
| 2008/2009 | Softball | | | Girls | Collège Stonewall Collegiate Rams | |
| 2007/2008 | Softball | | | Girls | Portage Collegiate Institute Saints | |
| 2006/2007 | Softball | | | Girls | Vincent Massey High School Vikings |  |
| 2005/2006 | Softball | | | Girls | Morden Collegiate Institute Thunder |  |
| 2004/2005 | Softball | | | Girls | Arthur Meighen High School Saints and Squires | |
| 2003/2004 | Softball | | | Girls | Major Pratt School Trojans |  |
| 2002/2003 | Softball | | | Girls | Major Pratt School Trojans | |
| 2001/2002 | Softball | | | Girls | École Secondaire Oak Park High School Raiders |  |
| 2000/2001 | Softball | | | Girls | Vincent Massey High School Vikings | |
| 1999/2000 | Softball | | | Girls | | |
| 1998/1999 | Softball | | | Girls | Morden Collegiate Institute Thunder | |
| 1997/1998 | Softball | | | Girls | St. Mary's Academy Flames |  |
| 1996/1997 | Softball | | | Girls | Virden Collegiate Institute Golden Bears |  |
| 1996/1997 | Softball | | | Boys | Landmark Collegiate 96ers |  |
| 1995/1996 | Softball | | | Girls | Swan Valley Regional Secondary School Tigers |  |
| 1995/1996 | Softball | | | Boys | Landmark Collegiate 96ers | |
| 1994/1995 | Softball | | | Girls | École Secondaire Oak Park High School Raiders | |
| 1994/1995 | Softball | | | Boys | Garden Valley Collegiate Zodiacs |  |
| 1993/1994 | Softball | | | Girls | École Secondaire Oak Park High School Raiders | |
| 1993/1994 | Softball | | | Boys | Garden Valley Collegiate Zodiacs | |
| 1992/1993 | Softball | | | Girls | École Secondaire Oak Park High School Raiders | |
| 1992/1993 | Softball | | | Boys | Hapnot Collegiate Institute Kopper Kings |  |
| 1991/1992 | Softball | | | Girls | Rivers Collegiate Rams |  |
| 1991/1992 | Softball | | | Boys | Landmark Collegiate 96ers | |
| 1990/1991 | Softball | | | Girls | École Secondaire Oak Park High School Raiders | |
| 1990/1991 | Softball | | | Boys | Landmark Collegiate 96ers | |
| 1989/1990 | Softball | | | Girls | École Secondaire Oak Park High School Raiders | |
| 1989/1990 | Softball | | | Boys | Hapnot Collegiate Institute Kopper Kings | |
| 1988/1989 | Softball | | | Girls | École Secondaire Oak Park High School Raiders | |
| 1988/1989 | Softball | | | Boys | Landmark Collegiate 96ers | |
| 1987/1988 | Softball | | | Girls | École régionale Notre-Dame Coyotes |  |
| 1987/1988 | Softball | | | Boys | Swan Valley Regional Secondary School Tigers | |
| 1986/1987 | Softball | | | Girls | | |
| 1986/1987 | Softball | | | Boys | Hapnot Collegiate Institute Kopper Kings | |
| 1985/1986 | Softball | | | Girls | Reston School Tigers | -c_40x40.png) |
| 1985/1986 | Softball | | | Boys | Hapnot Collegiate Institute Kopper Kings | |
| 1984/1985 | Softball | | | Girls | Teulon Collegiate Institute Saints |  |
| 1984/1985 | Softball | | | Boys | Hapnot Collegiate Institute Kopper Kings | |
| 1983/1984 | Softball | | | Girls | Ashern Central School Cobras |  |
| 1983/1984 | Softball | | | Boys | École Secondaire Sisler High School Spartans |  |
| 1981/1982 | Softball | | | Girls | Carman Collegiate Cougars |  |
| 1981/1982 | Softball | | | Boys | Garden Valley Collegiate Zodiacs | |
| 1980/1981 | Softball | | | Girls | Vincent Massey High School Vikings | |
| 1980/1981 | Softball | | | Boys | Gilbert Plains Collegiate Trojans |  |
| 1970/1971 | Softball | | | Girls | Teulon Collegiate Institute Saints | |
| 1970/1971 | Softball | | | Boys | Hartney School Hornets |  |
| 1969/1970 | Softball | | | Boys | Silver Heights Collegiate Huskies | |
