Thomas Spearman Past Winners Back to Trophies
2016-2017 Winner John Osborn #2
| Year | To | Team |
| 2017 | 2018 | |
| 2016 | 2017 | John Osborn #2 |
| 2015 | 2016 | St James #1 |
| 2014 | 2015 | Eddy's |
| 2013 | 2014 |
Assiniboia #1 (Formerly John Osborn #2) |
| 2012 | 2013 | Norwood #1 |
| 2011 | 2012 | Norwood #1 |
| 2010 | 2011 | Eddy's |
| 2009 | 2010 | Norwood #1 |
| 2008 | 2009 | Rockwood #2 |
| 2007 | 2008 |
W.S.O #1 (Formerly - Fort Rouge #1 ) |
| 2006 | 2007 | Norwood #1 |
| 2005 | 2006 | Bourbon St |
| 2004 | 2005 | Norwood |
| 2003 | 2004 | St James #2 |
| 2002 | 2003 | St James #2 |
| 2001 | 2002 | Norwood #2 |
| 2000 | 2001 | Norwood #1 |
| 1999 | 2000 | Fort Rouge #1 |
| 1998 | 1999 | |
| 1997 | 1998 | |
| 1996 | 1997 | |
| 1995 | 1996 | |
| 1994 | 1995 | |
| 1993 | 1994 | |
| 1992 | 1993 | |
| 1991 | 1992 | Norwood #2 |
| 1990 | 1991 | |
| 1989 | 1990 | |
| 1988 | 1989 | Imperial Vets |