Wins  | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 3 | |  Riley Beauchemin (F) | 1997 | | - |
| 2 | | Dan Delorme (F) | - | | - |
| 1 | | Dean Gorchynski (F) | 2003 | Winnipeg, MB, CAN | - |
| 1 | | Peyton Bateman (F) | 2004 | Stonewall, MB, CAN | - |
| 1 | | Rory Neill (D) | 2003 | Winnipeg, MB, CAN | - |
| 1 | | T.J. Matuszewski (F) | 2000 | Winkler, MB, CAN | - |
| 1 | | Elijah Carels (F) | 1999 | Bruxelles, MB, CAN | - |
| 1 | | Tanner Magalas (F) | 1995 | Winnipeg, MB, CAN | - |
| 1 | | Nick Doyle (F) | 1993 | Winnipeg, MB, CAN | - |
| 1 | | Brett Charette (F) | 1993 | Winnipeg, MB, CAN | - |
| 1 | | Cam Fehr (F) | 1993 | | - |
| 1 | | Mackenzie Acheson (F) | 1990 | Winnipeg, MB, CAN | - |
| 1 | | Eric Beaudin (F) | 1990 | Winnipeg, MB, CAN | - |
| 1 | | Colin Hekle (F) | 1988 | Winnipeg, MB, CAN | - |
| 1 | | Jason Frykas (F) | 1987 | Winnipeg, MB, CAN | - |
| 1 | | Scott Wagner (F) | 1987 | Winnipeg, MB, CAN | - |
| 1 | | Andrew Jensen (G) | - | MB, CAN | - |
| 1 | | Adam Kirk (F) | 1984 | Stonewall, MB, CAN | - |
| 1 | | Reggie Bilodeau (F) | - | | - |
| 1 | | Justin Carloni (G) | - | MB, CAN | - |
| 1 | | Eston Silver (F) | - | | - |
| 1 | | Justin Steeves (F) | - | | - |
| 1 | | Reggie Goodfellow (F) | - | MB, CAN | - |
| 1 | | Bob MacGregor (F) | - | | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 24-25 | | Dean Gorchynski (F) | 2003 | Winnipeg, MB, CAN | - |
| 23-24 | | Peyton Bateman (F) | 2004 | Stonewall, MB, CAN | - |
| 22-23 | | Rory Neill (D) | 2003 | Winnipeg, MB, CAN | - |
| 21-22 | | T.J. Matuszewski (F) | 2000 | Winkler, MB, CAN | - |
| 19-20 | | Elijah Carels (F) | 1999 | Bruxelles, MB, CAN | - |
| 18-19 | | Riley Beauchemin (F) | 1997 | | - |
| 17-18 | | Riley Beauchemin (F) | 1997 | | - |
| 16-17 | | Riley Beauchemin (F) | 1997 | | - |
| 15-16 | | Tanner Magalas (F) | 1995 | Winnipeg, MB, CAN | - |
| 14-15 | | Nick Doyle (F) | 1993 | Winnipeg, MB, CAN | - |
| 13-14 | | Brett Charette (F) | 1993 | Winnipeg, MB, CAN | - |
| 12-13 | | Cam Fehr (F) | 1993 | | - |
| 11-12 | | Mackenzie Acheson (F) | 1990 | Winnipeg, MB, CAN | - |
| 10-11 | | Eric Beaudin (F) | 1990 | Winnipeg, MB, CAN | - |
| 09-10 | | Colin Hekle (F) | 1988 | Winnipeg, MB, CAN | - |
| 08-09 | | Jason Frykas (F) | 1987 | Winnipeg, MB, CAN | - |
| 07-08 | | Scott Wagner (F) | 1987 | Winnipeg, MB, CAN | - |
| 06-07 | | Andrew Jensen (G) | - | MB, CAN | - |
| 05-06 | | Adam Kirk (F) | 1984 | Stonewall, MB, CAN | - |
| 04-05 | | Reggie Bilodeau (F) | - | | - |
| 03-04 | | Justin Carloni (G) | - | MB, CAN | - |
| 02-03 | | Eston Silver (F) | - | | - |
| 01-02 | | Justin Steeves (F) | - | | - |
| 00-01 | | Reggie Goodfellow (F) | - | MB, CAN | - |
| 99-00 | | Bob MacGregor (F) | - | | - |
| 98-99 | | Dan Delorme (F) | - | | - |
| 97-98 | | Dan Delorme (F) | - | | - |
