| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Kyle Ross (F) | 1986 | Regina, SK, CAN | - |
| 2 | | Blair St. Martin (D) | 1977 | Slave Lake, AB, CAN | - |
| 1 | | Blake Gustafson (D) | 2002 | Ardrossan, AB, CAN | - |
| 1 | | Dawson Holt (F) | 1999 | Saskatoon, SK, CAN | - |
| 1 | | Connor Blake (D) | 1998 | Calgary, AB, CAN | - |
| 1 | | Keaton Jameson (F) | 1997 | Brandon, MB, CAN | - |
| 1 | | Adam Henry (D) | 1994 | Winnipeg, MB, CAN | - |
| 1 | | Riley Kieser (F) | 1993 | Edmonton, AB, CAN | - |
| 1 | | Kendall McFaull (D) | 1992 | Rosetown, SK, CAN | Atlanta Thrashers (2010) |
| 1 | | Drydn Dow (D) | 1992 | Calgary, AB, CAN | - |
| 1 | | Dylan Tait (G) | 1991 | Lethbridge, AB, CAN | - |
| 1 | | Jordan DePape (F) | 1992 | Winnipeg, MB, CAN | - |
| 1 | | Ben Lindemulder (D) | 1988 | Edmonton, AB, CAN | - |
| 1 | | Greg Gardner (F) | 1987 | Cold Lake, AB, CAN | - |
| 1 | | Tyler Metcalfe (F) | 1984 | Headingley, MB, CAN | - |
| 1 | | Curtis Austring (F) | 1982 | Stewart Valley, SK, CAN | - |
| 1 | | Jay Langager (D) | 1980 | Loreburn, SK, CAN | - |
| 1 | | Paul Deniset (F) | 1981 | Winnipeg, MB, CAN | - |
| 1 | | Gavin McLeod (D) | 1980 | Delta, BC, CAN | Ottawa Senators (1998) |
| 1 | | Jeff Zorn (D) | 1979 | Tisdale, SK, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 24-25 | | Blake Gustafson (D) | 2002 | Ardrossan, AB, CAN | - |
| 23-24 | | Dawson Holt (F) | 1999 | Saskatoon, SK, CAN | - |
| 22-23 | | Connor Blake (D) | 1998 | Calgary, AB, CAN | - |
| 21-22 | | Keaton Jameson (F) | 1997 | Brandon, MB, CAN | - |
| 19-20 | | Adam Henry (D) | 1994 | Winnipeg, MB, CAN | - |
| 18-19 | | Riley Kieser (F) | 1993 | Edmonton, AB, CAN | - |
| 17-18 | | Kendall McFaull (D) | 1992 | Rosetown, SK, CAN | Atlanta Thrashers (2010) |
| 16-17 | | Drydn Dow (D) | 1992 | Calgary, AB, CAN | - |
| 15-16 | | Dylan Tait (G) | 1991 | Lethbridge, AB, CAN | - |
| 14-15 | | Jordan DePape (F) | 1992 | Winnipeg, MB, CAN | - |
| 13-14 | | Ben Lindemulder (D) | 1988 | Edmonton, AB, CAN | - |
| 12-13 | | Greg Gardner (F) | 1987 | Cold Lake, AB, CAN | - |
| 11-12 | | Kyle Ross (F) | 1986 | Regina, SK, CAN | - |
| 09-10 | | Tyler Metcalfe (F) | 1984 | Headingley, MB, CAN | - |
| 08-09 | | Kyle Ross (F) | 1986 | Regina, SK, CAN | - |
| 07-08 | | Curtis Austring (F) | 1982 | Stewart Valley, SK, CAN | - |
| 06-07 | | Jay Langager (D) | 1980 | Loreburn, SK, CAN | - |
| 05-06 | | Paul Deniset (F) | 1981 | Winnipeg, MB, CAN | - |
| 04-05 | | Gavin McLeod (D) | 1980 | Delta, BC, CAN | Ottawa Senators (1998) |
| 03-04 | | Jeff Zorn (D) | 1979 | Tisdale, SK, CAN | - |
| 02-03 | | Blair St. Martin (D) | 1977 | Slave Lake, AB, CAN | - |
| 01-02 | | Blair St. Martin (D) | 1977 | Slave Lake, AB, CAN | - |
