| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 3 | 31 |  Curtis Gardham (F) | 1990 | Arrow River, MB, CAN | - |
| 3 | 55 | Pat Falloon (F) | 1972 | Foxwarren, MB, CAN | San Jose Sharks (1991) |
| 2 | 29 | Taylor Sanheim (F) | 1996 | Elkhorn, MB, CAN | - |
| 2 | 41 | Brian Kostur (F) | 1975 | Gilbert Plains, MB, CAN | - |
| 2 | 56 | Derek Tibbatts (F) | 1973 | Foxwarren, MB, CAN | - |
| 1 | 19 | Brayden Nabholz (F) | - | | - |
| 1 | 26 | Tanner Lewis (F) | 1996 | Virden, MB, CAN | - |
| 1 | 31 | Ryan Dreger (F) | 1989 | Dauphin, MB, CAN | - |
| 1 | 29 | Kyle McLeod (F) | 1992 | Elkhorn, MB, CAN | - |
| 1 | 34 | Steegan Stoski (F) | 1985 | Gilbert Plains, MB, CAN | - |
| 1 | 29 | Taras Turko (F) | - | MB, CAN | - |
| 1 | 32 | Luke Stokotelny (F) | 1988 | Dauphin, MB, CAN | - |
| 1 | 24 | Ryan Halliday (F) | 1987 | Brandon, MB, CAN | - |
| 1 | 31 | Danny Johnston (F) | 1983 | Foxwarren, MB, CAN | - |
| 1 | 54 | Ted Fleury (F) | 1970 | Williams Lake, BC, CAN | - |
| 1 | 34 | Troy Stewart (F) | 1978 | Kenton, MB, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 21-22 | 29 | Taylor Sanheim (F) | 1996 | Elkhorn, MB, CAN | - |
| 19-20 | 28 | Taylor Sanheim (F) | 1996 | Elkhorn, MB, CAN | - |
| 18-19 | 19 | Brayden Nabholz (F) | - | | - |
| 17-18 | 26 | Tanner Lewis (F) | 1996 | Virden, MB, CAN | - |
| 16-17 | 31 | Curtis Gardham (F) | 1990 | Arrow River, MB, CAN | - |
| 15-16 | 24 | Curtis Gardham (F) | 1990 | Arrow River, MB, CAN | - |
| 14-15 | 31 | Ryan Dreger (F) | 1989 | Dauphin, MB, CAN | - |
| 13-14 | 29 | Kyle McLeod (F) | 1992 | Elkhorn, MB, CAN | - |
| 12-13 | 34 | Steegan Stoski (F) | 1985 | Gilbert Plains, MB, CAN | - |
| 11-12 | 29 | Taras Turko (F) | - | MB, CAN | - |
| 10-11 | 31 | Curtis Gardham (F) | 1990 | Arrow River, MB, CAN | - |
| 09-10 | 32 | Luke Stokotelny (F) | 1988 | Dauphin, MB, CAN | - |
| 08-09 | 24 | Ryan Halliday (F) | 1987 | Brandon, MB, CAN | - |
| 07-08 | 31 | Danny Johnston (F) | 1983 | Foxwarren, MB, CAN | - |
| 06-07 | 41 | Brian Kostur (F) | 1975 | Gilbert Plains, MB, CAN | - |
| 05-06 | 44 | Pat Falloon (F) | 1972 | Foxwarren, MB, CAN | San Jose Sharks (1991) |
| 04-05 | 32 | Brian Kostur (F) | 1975 | Gilbert Plains, MB, CAN | - |
| 04-05 | 32 | Derek Tibbatts (F) | 1973 | Foxwarren, MB, CAN | - |
| 03-04 | 55 | Pat Falloon (F) | 1972 | Foxwarren, MB, CAN | San Jose Sharks (1991) |
| 02-03 | 47 | Pat Falloon (F) | 1972 | Foxwarren, MB, CAN | San Jose Sharks (1991) |
| 01-02 | 56 | Derek Tibbatts (F) | 1973 | Foxwarren, MB, CAN | - |
| 00-01 | 54 | Ted Fleury (F) | 1970 | Williams Lake, BC, CAN | - |
| 99-00 | 34 | Troy Stewart (F) | 1978 | Kenton, MB, CAN | - |
