John (Jock) Milton Past Winners Back to Trophies
2016-2017 Winner Charleswood #2
| Year | To | Team |
| 2017 | 2018 | |
| 2016 | 2017 | Charleswood #2 |
| 2015 | 2016 | Norwood #2 |
| 2014 | 2015 | Charleswood |
| 2013 | 2014 | St James #1 |
| 2012 | 2013 | Assiniboia #2 |
| 2011 | 2012 | Eddy's |
| 2010 | 2011 | Norwood #2 |
| 2009 | 2010 | Norwood #2 |
| 2008 | 2009 |
W.S.O #2 (Formerly - Fort Rouge #2 ) |
| 2007 | 2008 | John Osborn #1 |
| 2006 | 2007 | Rockwood |
| 2005 | 2006 | Rockwood |
| 2004 | 2005 | St James #2 |
| 2003 | 2004 | Norwood |
| 2002 | 2003 | Norwood #2 |
| 2001 | 2002 | Bourbon St |
| 2000 | 2001 | Fort Rouge #1 |
| 1999 | 2000 | St James #2 |
| 1998 | 1999 | Rockwood |
| 1997 | 1998 | John Osborn #1 |
| 1996 | 1997 | Imperial Vets |
| 1995 | 1996 | Garry St |
| 1994 | 1995 | John Osborn #1 |
| 1993 | 1994 | Imperial Vets |
| 1992 | 1993 | St James |
| 1991 | 1992 | |
| 1990 | 1991 | Fort Rouge #2 |
| 1989 | 1990 | St James #1 |
| 1988 | 1989 | St James #1 |
| 1987 | 1988 | Winnipeg #1 |
| 1986 | 1987 | St James #1 |
| 1985 | 1986 | Charleswood |
| 1984 | 1985 | Fort Rouge |
| 1983 | 1984 | Assiniboia #2 |
| 1982 | 1983 | Rockwood |
| 1981 | 1982 | Charleswood |
| 1980 | 1981 | |
| 1979 | 1980 | St Georges #2 |
| 1978 | 1979 | Winnipeg |
| 1977 | 1978 | St James #2 |
| 1976 | 1977 | St Georges #2 |
| 1975 | 1976 | Fort Rouge |
| 1974 | 1975 | |
| 1973 | 1974 | |
| 1972 | 1973 | |
| 1971 | 1972 | Young St |
| 1970 | 1971 | Fort Rouge #2 |
| 1969 | 1970 | St Vital |
