| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Denis Gagnon (D) | 2002 | Ste. Agathe, MB, CAN | - |
| 2 | | Kale Price (F) | 2002 | Winnipeg, MB, CAN | - |
| 2 | | Dylan Arnold (G) | 2001 | Winnipeg, MB, CAN | - |
| 2 | | Brady Whitely (D) | 2002 | Winnipeg, MB, CAN | - |
| 2 | | Jeremy Idzikowski (D) | 1997 | Winnipeg, MB, CAN | - |
| 2 | | Matt Kohlman (G) | 1995 | McCreary, MB, CAN | - |
| 1 | | Ashton Howarth (G) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Cameron McDonald (F) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Tyler Rubigny (F) | 2003 | Winnipeg, MB, CAN | - |
| 1 | | Rhonan White (D) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Noah Gilbert (G) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Matthew Smith (F) | 2001 | Beausejour, MB, CAN | - |
| 1 | | Levi Thiessen (F) | 2002 | Winnipeg, MB, CAN | - |
| 1 | | Riley Barroso (F) | 2000 | Winnipeg, MB, CAN | - |
| 1 | | Devin Bulloch (D) | 2000 | MB, CAN | - |
| 1 | | Conner Grunsten (F) | 2000 | Winnipeg, MB, CAN | - |
| 1 | | Ethan Lewis (F) | 2001 | Winnipeg, MB, CAN | - |
| 1 | | Keeven Daniels-Webb (F) | 1999 | Peguis, MB, CAN | - |
| 1 | | Tyson Last (F) | 1998 | Winnipeg, MB, CAN | - |
| 1 | | Ben Orris (D) | 1998 | | - |
| 1 | | Adam Thurlbeck (D) | 1998 | Winnipeg, MB, CAN | - |
| 1 | | Cole Zadro (F) | 1998 | Winnipeg, MB, CAN | - |
| 1 | | Jeremie Goderis (F) | 1999 | Swan Lake, MB, CAN | - |
| 1 | | Travis Penner (F) | 2000 | LaSalle, MB, CAN | - |
| 1 | | Jeremy Pikel (G) | 2000 | | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 23-24 | | Ashton Howarth (G) | 2002 | Winnipeg, MB, CAN | - |
| 23-24 | | Denis Gagnon (D) | 2002 | Ste. Agathe, MB, CAN | - |
| 23-24 | | Rhonan White (D) | 2002 | Winnipeg, MB, CAN | - |
| 23-24 | | Kale Price (F) | 2002 | Winnipeg, MB, CAN | - |
| 23-24 | | Tyler Rubigny (F) | 2003 | Winnipeg, MB, CAN | - |
| 23-24 | | Cameron McDonald (F) | 2002 | Winnipeg, MB, CAN | - |
| 22-23 | | Noah Gilbert (G) | 2002 | Winnipeg, MB, CAN | - |
| 22-23 | | Denis Gagnon (D) | 2002 | Ste. Agathe, MB, CAN | - |
| 22-23 | | Brady Whitely (D) | 2002 | Winnipeg, MB, CAN | - |
| 22-23 | | Kale Price (F) | 2002 | Winnipeg, MB, CAN | - |
| 22-23 | | Matthew Smith (F) | 2001 | Beausejour, MB, CAN | - |
| 22-23 | | Levi Thiessen (F) | 2002 | Winnipeg, MB, CAN | - |
| 21-22 | | Dylan Arnold (G) | 2001 | Winnipeg, MB, CAN | - |
| 21-22 | | Devin Bulloch (D) | 2000 | MB, CAN | - |
| 21-22 | | Brady Whitely (D) | 2002 | Winnipeg, MB, CAN | - |
| 21-22 | | Riley Barroso (F) | 2000 | Winnipeg, MB, CAN | - |
| 21-22 | | Conner Grunsten (F) | 2000 | Winnipeg, MB, CAN | - |
| 21-22 | | Ethan Lewis (F) | 2001 | Winnipeg, MB, CAN | - |
| 19-20 | | Dylan Arnold (G) | 2001 | Winnipeg, MB, CAN | - |
| 19-20 | | Ben Orris (D) | 1998 | | - |
| 19-20 | | Adam Thurlbeck (D) | 1998 | Winnipeg, MB, CAN | - |
| 19-20 | | Tyson Last (F) | 1998 | Winnipeg, MB, CAN | - |
| 19-20 | | Cole Zadro (F) | 1998 | Winnipeg, MB, CAN | - |
| 19-20 | | Keeven Daniels-Webb (F) | 1999 | Peguis, MB, CAN | - |
| 18-19 | | Jeremy Pikel (G) | 2000 | | - |
| 18-19 | | Jeremy Idzikowski (D) | 1997 | Winnipeg, MB, CAN | - |
| 18-19 | | Jeremie Goderis (F) | 1999 | Swan Lake, MB, CAN | - |
| 18-19 | | Travis Penner (F) | 2000 | LaSalle, MB, CAN | - |
| 18-19 | | Tyler Slobogian (F) | 1997 | | - |
| 17-18 | | Connor Shaw (G) | 1996 | Dauphin, MB, CAN | - |
| 17-18 | | Eli Batt (D) | 1996 | Winnipeg, MB, CAN | - |
| 17-18 | | Jeremy Idzikowski (D) | 1997 | Winnipeg, MB, CAN | - |
| 17-18 | | Nicolas Burmey (F) | 1998 | Winnipeg, MB, CAN | - |
| 17-18 | | Tyler Meixner (F) | 1997 | Winnipeg, MB, CAN | - |
| 17-18 | | Carson Rybuck (F) | 1996 | Winnipeg, MB, CAN | - |
| 16-17 | | Matt Kohlman (G) | 1995 | McCreary, MB, CAN | - |
| 16-17 | | Riley Gilmore (D) | 1996 | | - |
| 16-17 | | Graham Philp (D) | 1995 | | - |
| 16-17 | | Zach Heisinger (F) | 1995 | Winnipeg, MB, CAN | - |
| 16-17 | | Mitchell Lockhart (F) | 1995 | Winnipeg, MB, CAN | - |
| 16-17 | | Corey Mazinke (F) | 1995 | Morris, MB, CAN | - |
| 15-16 | | Brenden Fiebelkorn (G) | 1994 | Winnipeg, MB, CAN | - |
| 15-16 | | Garrett Bruce (D) | 1995 | Stonewall, MB, CAN | - |
| 15-16 | | Tyson Bannatyne (D) | 1995 | | - |
| 15-16 | | Jens Giesbrecht (F) | 1995 | | - |
| 15-16 | | Nick Matthews (F) | 1996 | Winnipeg, MB, CAN | - |
| 15-16 | | Justin Tremblay (F) | 1995 | | - |
| 14-15 | | Matt Kohlman (G) | 1995 | McCreary, MB, CAN | - |
| 14-15 | | Sean Christensen (D) | 1993 | Winnipeg, MB, CAN | - |
| 14-15 | | Macauley Siemens (D) | 1993 | Oak Bluff, MB, CAN | - |
| 14-15 | | Brett Charette (F) | 1993 | Winnipeg, MB, CAN | - |
| 14-15 | | Simon Miller (F) | 1993 | Winnipeg, MB, CAN | - |
| 14-15 | | Greg Myall (F) | 1993 | Winnipeg, MB, CAN | - |
