| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 3 | |  Riley Beauchemin (F) | 1997 | | - |
| 2 | | Tyrone Willan (F) | 2002 | Winnipeg, MB, CAN | - |
| 2 | | Rory Neill (D) | 2003 | Winnipeg, MB, CAN | - |
| 2 | | Ryan Hall (G) | 1998 | Winnipeg, MB, CAN | - |
| 2 | | Chase Faulkner (F) | 1996 | Stonewall, MB, CAN | - |
| 2 | | Nicolas Gravel (D) | 1996 | Lorette, MB, CAN | - |
| 2 | | Isaac Bellan (D) | 1994 | | - |
| 2 | | Riley Kuryk (D) | 1994 | Winnipeg, MB, CAN | - |
| 2 | | Danick Levesque (F) | 1994 | | - |
| 2 | | Tanner Magalas (F) | 1995 | Winnipeg, MB, CAN | - |
| 1 | | Noah Gilbert (G) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Ryland Hueging (F) | 2003 | MB, CAN | - |
| 1 | | Sam Mitani (D) | 2003 | Winnipeg, MB, CAN | - |
| 1 | | Brady Whitely (D) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Derek Wiebe (F) | 2002 | Morden, MB, CAN | - |
| 1 | | Mattie Boonstra (F) | 2001 | Garson, ON, CAN | - |
| 1 | | Ashton Howarth (G) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Tyler Rubigny (F) | 2003 | Winnipeg, MB, CAN | - |
| 1 | | Conrad Solypa (D) | 2001 | Cooks Creek, MB, CAN | - |
| 1 | | Alec Borger (D) | 2000 | Winnipeg, MB, CAN | - |
| 1 | | Ben Coppinger (F) | 2000 | Winnipeg, MB, CAN | - |
| 1 | | Kurtis Luke (D) | 2000 | Ste. Rose, MB, CAN | - |
| 1 | | T.J. Matuszewski (F) | 2000 | Winkler, MB, CAN | - |
| 1 | | Miles Minor (G) | 2000 | Winnipeg, MB, CAN | - |
| 1 | | Jared Bucci (F) | 1999 | Winnipeg, MB, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 23-24 | | Noah Gilbert (G) | 2002 | Winnipeg, MB, CAN | - |
| 23-24 | | Sam Mitani (D) | 2003 | Winnipeg, MB, CAN | - |
| 23-24 | | Brady Whitely (D) | 2002 | Winnipeg, MB, CAN | - |
| 23-24 | | Derek Wiebe (F) | 2002 | Morden, MB, CAN | - |
| 23-24 | | Tyrone Willan (F) | 2002 | Winnipeg, MB, CAN | - |
| 23-24 | | Ryland Hueging (F) | 2003 | MB, CAN | - |
| 22-23 | | Ashton Howarth (G) | 2002 | Winnipeg, MB, CAN | - |
| 22-23 | | Rory Neill (D) | 2003 | Winnipeg, MB, CAN | - |
| 22-23 | | Conrad Solypa (D) | 2001 | Cooks Creek, MB, CAN | - |
| 22-23 | | Mattie Boonstra (F) | 2001 | Garson, ON, CAN | - |
| 22-23 | | Tyler Rubigny (F) | 2003 | Winnipeg, MB, CAN | - |
| 22-23 | | Tyrone Willan (F) | 2002 | Winnipeg, MB, CAN | - |
| 21-22 | | Miles Minor (G) | 2000 | Winnipeg, MB, CAN | - |
| 21-22 | | Alec Borger (D) | 2000 | Winnipeg, MB, CAN | - |
| 21-22 | | Rory Neill (D) | 2003 | Winnipeg, MB, CAN | - |
| 21-22 | | Kurtis Luke (D) | 2000 | Ste. Rose, MB, CAN | - |
| 21-22 | | T.J. Matuszewski (F) | 2000 | Winkler, MB, CAN | - |
| 21-22 | | Ben Coppinger (F) | 2000 | Winnipeg, MB, CAN | - |
| 19-20 | | Luke Zacharias (G) | 1998 | Minnedosa, MB, CAN | - |
| 19-20 | | Spencer Ferbers (D) | 1998 | Winnipeg, MB, CAN | - |
| 19-20 | | Jared Hulme (D) | 1999 | MacGregor, MB, CAN | - |
| 19-20 | | Jared Bucci (F) | 1999 | Winnipeg, MB, CAN | - |
| 19-20 | | Elijah Carels (F) | 1999 | Bruxelles, MB, CAN | - |
| 19-20 | | Cedric Chenier (F) | 2000 | Winnipeg, MB, CAN | - |
| 18-19 | | Ryan Hall (G) | 1998 | Winnipeg, MB, CAN | - |
| 18-19 | | Braden Groot (D) | 1997 | Stonewall, MB, CAN | - |
| 18-19 | | Derek Wood (D) | 1997 | Graysville, MB, CAN | - |
| 18-19 | | Riley Beauchemin (F) | 1997 | | - |
| 18-19 | | Braeden Beernaerts (F) | 1997 | Swan Lake, MB, CAN | - |
| 18-19 | | Noah Skorpad (F) | 1998 | | - |
| 17-18 | | Ryan Hall (G) | 1998 | Winnipeg, MB, CAN | - |
| 17-18 | | Riley Gilmore (D) | 1996 | | - |
| 17-18 | | Nicolas Gravel (D) | 1996 | Lorette, MB, CAN | - |
| 17-18 | | Riley Beauchemin (F) | 1997 | | - |
| 17-18 | | Chase Faulkner (F) | 1996 | Stonewall, MB, CAN | - |
| 17-18 | | Nick Matthews (F) | 1996 | Winnipeg, MB, CAN | - |
| 16-17 | | Hunter Ploszay (G) | 1996 | Stonewall, MB, CAN | - |
| 16-17 | | Nicolas Gravel (D) | 1996 | Lorette, MB, CAN | - |
| 16-17 | | K C Mason (D) | 1995 | | - |
| 16-17 | | Riley Beauchemin (F) | 1997 | | - |
| 16-17 | | Chase Faulkner (F) | 1996 | Stonewall, MB, CAN | - |
| 16-17 | | Mike Lorange (F) | 1995 | Winnipeg, MB, CAN | - |
| 15-16 | | Ben Thorlakson (G) | 1996 | | - |
| 15-16 | | Isaac Bellan (D) | 1994 | | - |
| 15-16 | | Riley Kuryk (D) | 1994 | Winnipeg, MB, CAN | - |
| 15-16 | | Danick Levesque (F) | 1994 | | - |
| 15-16 | | Mitchell Lockhart (F) | 1995 | Winnipeg, MB, CAN | - |
| 15-16 | | Tanner Magalas (F) | 1995 | Winnipeg, MB, CAN | - |
| 14-15 | | Brenden Fiebelkorn (G) | 1994 | Winnipeg, MB, CAN | - |
| 14-15 | | Isaac Bellan (D) | 1994 | | - |
| 14-15 | | Riley Kuryk (D) | 1994 | Winnipeg, MB, CAN | - |
| 14-15 | | Nick Doyle (F) | 1993 | Winnipeg, MB, CAN | - |
| 14-15 | | Danick Levesque (F) | 1994 | | - |
| 14-15 | | Tanner Magalas (F) | 1995 | Winnipeg, MB, CAN | - |
