| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Jerrod Auger (G) | 1986 | Russell, MB, CAN | - |
| 2 | | Joel Mateika (F) | 1986 | Miniota, MB, CAN | - |
| 2 | | Kyler Beckett (G) | 1994 | Moosemin, SK, CAN | - |
| 2 | | Andy Chipelski (D) | 1983 | Winnipeg, MB, CAN | - |
| 1 | | Jason Bowles (F) | 1988 | Elkhorn, MB, CAN | - |
| 1 | | Skyler Hladun (F) | 1992 | Canora, SK, CAN | - |
| 1 | | Brandon Masson (D) | 1996 | Oak Lake, MB, CAN | - |
| 1 | | Kaine Morran (D) | - | MB, CAN | - |
| 1 | | Brad Bowles (F) | 1995 | Elkhorn, MB, CAN | - |
| 1 | | Shawn Bowles (F) | 1995 | Elkhorn, MB, CAN | - |
| 1 | | Dustin Fisher (F) | 1982 | Carberry, MB, CAN | - |
| 1 | | Colin Paull (D) | 1990 | Elkhorn, MB, CAN | - |
| 1 | | Derek Falloon (F) | 1993 | Russell, MB, CAN | - |
| 1 | | Carey Findlay (D) | 1987 | Shoal Lake, MB, CAN | - |
| 1 | | Reagan Hedley (F) | 1992 | Virden, MB, CAN | - |
| 1 | | Brock Jersak (F) | 1989 | MB, CAN | - |
| 1 | | Bradley Potoroka (F) | 1993 | Dauphin, MB, CAN | - |
| 1 | | Adam Robidoux (D) | 1998 | Binscarth, MB, CAN | - |
| 1 | | Dallas Anderson (F) | 1979 | Bowsman, MB, CAN | - |
| 1 | | Jordan Cullum (F) | 1994 | Russell, MB, CAN | - |
| 1 | | Deven Dubyk (G) | 1991 | Minitonas, MB, CAN | - |
| 1 | | Nat Howard (F) | 1987 | Miniota, MB, CAN | - |
| 1 | | Darcy Riddell (F) | 1989 | Swan River, MB, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 19-20 | | Jerrod Auger (G) | 1986 | Russell, MB, CAN | - |
| 19-20 | | Brandon Masson (D) | 1996 | Oak Lake, MB, CAN | - |
| 19-20 | | Kaine Morran (D) | - | MB, CAN | - |
| 19-20 | | Jason Bowles (F) | 1988 | Elkhorn, MB, CAN | - |
| 19-20 | | Skyler Hladun (F) | 1992 | Canora, SK, CAN | - |
| 19-20 | | Joel Mateika (F) | 1986 | Miniota, MB, CAN | - |
| 18-19 | | Kyler Beckett (G) | 1994 | Moosemin, SK, CAN | - |
| 18-19 | | Andy Chipelski (D) | 1983 | Winnipeg, MB, CAN | - |
| 18-19 | | Colin Paull (D) | 1990 | Elkhorn, MB, CAN | - |
| 18-19 | | Brad Bowles (F) | 1995 | Elkhorn, MB, CAN | - |
| 18-19 | | Shawn Bowles (F) | 1995 | Elkhorn, MB, CAN | - |
| 18-19 | | Dustin Fisher (F) | 1982 | Carberry, MB, CAN | - |
| 17-18 | | Jerrod Auger (G) | 1986 | Russell, MB, CAN | - |
| 17-18 | | Kyler Beckett (G) | 1994 | Moosemin, SK, CAN | - |
| 17-18 | | Andy Chipelski (D) | 1983 | Winnipeg, MB, CAN | - |
| 17-18 | | Carey Findlay (D) | 1987 | Shoal Lake, MB, CAN | - |
| 17-18 | | Adam Robidoux (D) | 1998 | Binscarth, MB, CAN | - |
| 17-18 | | Reagan Hedley (F) | 1992 | Virden, MB, CAN | - |
| 17-18 | | Derek Falloon (F) | 1993 | Russell, MB, CAN | - |
| 17-18 | | Brock Jersak (F) | 1989 | MB, CAN | - |
| 17-18 | | Bradley Potoroka (F) | 1993 | Dauphin, MB, CAN | - |
| 16-17 | | Deven Dubyk (G) | 1991 | Minitonas, MB, CAN | - |
| 16-17 | | Darcy Riddell (F) | 1989 | Swan River, MB, CAN | - |
| 16-17 | | Jordan Cullum (F) | 1994 | Russell, MB, CAN | - |
| 16-17 | | Nat Howard (F) | 1987 | Miniota, MB, CAN | - |
| 16-17 | | Dallas Anderson (F) | 1979 | Bowsman, MB, CAN | - |
| 16-17 | | Joel Mateika (F) | 1986 | Miniota, MB, CAN | - |
