Ken Vincent Past Winners Back to Trophies
2016-2017 Winner Kevin Augusta
| Year | To | Player | Team |
| 2017 | 2018 | ||
| 2016 | 2017 | Kevin Augusta | John Osborn #2 |
| 2015 | 2016 | Steve Kingyens | Norwood #2 |
| 2014 | 2015 | Fraser Durham | Norwood #1 |
| 2013 | 2014 | Rick Hutcheon | Norwood #2 |
| 2012 | 2013 | Rick Kendall | St James #2 |
| 2011 | 2012 | Guy Smith |
W.S.O #1 (Formerly - Fort Rouge #1 ) |
| 2010 | 2011 | Al Senkiw | St James #1 |
| 2009 | 2010 | Steve Jones | St James #2 |
| 2008 | 2009 | Rick Kendall | St James |
| 2007 | 2008 | Dave Blacklaw |
W.S.O #2 (Formerly - Fort Rouge #2 ) |
| 2006 | 2007 | Pat Werner | Rockwood |
| 2005 | 2006 | Jim Harvey | Rockwood |
| 2004 | 2005 | Fred McGillivray | Norwood |
| 2003 | 2004 | Bill Smith | Fort Rouge #2 |
| 2002 | 2003 | Warren Dyer | St James #2 |
| 2001 | 2002 | Jules Mortinson | Norwood #1 |
| 2000 | 2001 | Guy Smith | Fort Rouge #1 |
| 1999 | 2000 | Fraser Durham | Imperial Vets |
| 1998 | 1999 |
Garry Marshall Kevin Corrigan |
Imperial Vets Imperial Vets |
| 1997 | 1998 | Mike Balork | Norwood |
| 1996 | 1997 | Fraser Durham | Imperial Vets |
| 1995 | 1996 | Kevin Corrigan | Imperial Vets |
| 1994 | 1995 | Rob Klem | Norwood #2 |
| 1993 | 1994 | Al Senkiw | Imperial Vets |