| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Baron Baker (D) | 2006 | MB, CAN | - |
| 2 | | Kale Chipman (D) | 2006 | MB, CAN | - |
| 2 | | Jaxson Fillion (F) | 2006 | MB, CAN | - |
| 2 | | Dylan Jaquet (F) | 2006 | MB, CAN | - |
| 2 | | Lukas Mager (F) | 2006 | MB, CAN | - |
| 2 | | Leyton Medwick (G) | 2006 | MB, CAN | - |
| 2 | | Matthew O'Sullivan (F) | 2006 | Winnipeg, MB, CAN | - |
| 2 | | Matthew Sawchyn (D) | 2006 | | - |
| 2 | | Connor Vandal (F) | 2007 | Winnipeg, MB, CAN | - |
| 2 | | Ethan Clements (F) | 2003 | Winnipeg, MB, CAN | - |
| 2 | | Hayden Forrest (D) | 2002 | Winnipeg, MB, CAN | - |
| 2 | | Nolan Male (D) | 2002 | Winnipeg, MB, CAN | - |
| 2 | | Anton Uruski (D) | 2002 | Winnipeg, MB, CAN | - |
| 2 | | Ryan Brennan (D) | 2001 | Winnipeg, MB, CAN | - |
| 2 | | Brayden Foreman (F) | 2001 | Winnipeg, MB, CAN | - |
| 2 | | Duncan Jowett (D) | 2001 | Winnipeg, MB, CAN | - |
| 2 | | Dimitri Mattheos (D) | 2001 | Winnipeg, MB, CAN | - |
| 2 | | Evan Van Laeken (G) | 2001 | Winnipeg, MB, CAN | - |
| 2 | | Bowan Spence (D) | 2000 | Winnipeg, MB, CAN | - |
| 1 | | Ty Aldcroft (F) | 2009 | | - |
| 1 | | Cashton Chastellaine (F) | - | Brandon, MB, CAN | - |
| 1 | | Ethan Chen (F) | - | Brandon, MB, CAN | - |
| 1 | | Ty Cowan (D) | 2009 | | - |
| 1 | | Jaxon Deg (F) | - | | - |
| 1 | | Carson Fowler (F) | - | Brandon, MB, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 25-26 | | Carter Krahn (G) | 2010 | Winnipeg, MB, CAN | - |
| 25-26 | | Zayden Munro (G) | 2010 | Brandon, MB, CAN | - |
| 25-26 | | Ty Cowan (D) | 2009 | | - |
| 25-26 | | Karter Hermenegildo (D) | 2009 | | - |
| 25-26 | | Vaughan Mcleod (D) | - | Brandon, MB, CAN | - |
| 25-26 | | Colin Melnyk (D) | 2010 | Forrest, MB, CAN | - |
| 25-26 | | Landon Redfern (D) | - | | - |
| 25-26 | | Grayson Rome (D) | - | Brandon, MB, CAN | - |
| 25-26 | | Ty Aldcroft (F) | 2009 | | - |
| 25-26 | | Cashton Chastellaine (F) | - | Brandon, MB, CAN | - |
| 25-26 | | Ethan Chen (F) | - | Brandon, MB, CAN | - |
| 25-26 | | Jaxon Deg (F) | - | | - |
| 25-26 | | Carson Fowler (F) | - | Brandon, MB, CAN | - |
| 25-26 | | Luke Krieser (F) | 2009 | Brandon, MB, CAN | - |
| 25-26 | | William Marvin (F) | 2010 | Brandon, MB, CAN | - |
| 25-26 | | Soren Milne (F) | - | | - |
| 25-26 | | Denzel Monias (F) | 2009 | | - |
| 25-26 | | Max Roberts (F) | - | | - |
| 25-26 | | Ashton Shields (F) | 2009 | | - |
| 25-26 | | Sullivan Taylor (F) | 2011 | Brandon, MB, CAN | - |
| 25-26 | | Etienne Visser (F) | 2010 | Brandon, MB, CAN | - |
| 25-26 | | Brayden Watt (F) | 2010 | Brandon, MB, CAN | - |
| 24-25 | | Noah Cesmystruk (G) | 2008 | | - |
| 24-25 | | Zachary Houtkooper (G) | 2009 | Winnipeg, MB, CAN | - |
| 24-25 | | Emil Bekerman (D) | 2009 | | - |
| 24-25 | | Ben den Teuling (D) | 2008 | Winnipeg, MB, CAN | - |
| 24-25 | | Holten Dorge (D) | 2009 | | - |
| 24-25 | | Dryden Fougere (D) | 2009 | | - |
| 24-25 | | Luka Gosselin (D) | 2008 | | - |
| 24-25 | | James Nicholls (F) | 2009 | Toronto, ON, CAN | - |
| 24-25 | | Mason Chubey (F) | 2009 | Winnipeg, MB, CAN | - |
| 24-25 | | Damian Dnes (F) | 2009 | | - |
| 24-25 | | Mitchell Hill (F) | 2008 | Winnipeg, MB, CAN | - |
| 24-25 | | Logan Jacobson (F) | 2009 | | - |
| 24-25 | | Triton Joudrey (F) | 2008 | | - |
| 24-25 | | Lucas Merner (F) | 2008 | | - |
| 24-25 | | Grant Newton (F) | 2009 | | - |
| 24-25 | | Will Owens (F) | 2010 | Winnipeg, MB, CAN | - |
| 24-25 | | Carson St. Lawrence (F) | 2009 | | - |
| 24-25 | | Trevor Toyne (F) | 2010 | | - |
| 24-25 | | Liam Ullrich (F) | 2009 | | - |
| 24-25 | | Joel Vermette (F) | 2009 | | - |
| 24-25 | | Ethan Walterson (F) | 2009 | | - |
| 24-25 | | Efrem Wolitski (F) | 2009 | | - |
| 23-24 | | Nolan Giles (G) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Zakary Matheson (G) | 2008 | London, ON, CAN | - |
| 23-24 | | Brady Bell (D) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Noah Bonds (D) | 2009 | | - |
| 23-24 | | Sandro Dell'Acqua (D) | 2007 | Winnipeg, MB, CAN | - |
| 23-24 | | Ethan Hulme (D) | 2007 | Winnipeg, MB, CAN | - |
| 23-24 | | Colin Krestanowich (D) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Elliott Ortlieb (D) | 2009 | Winnipeg, MB, CAN | - |
| 23-24 | | Ron Strilchuk (D) | - | | - |
| 23-24 | | Kaden Sutherland (D) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Trey Taylor (D) | 2008 | St. Mary's, ON, CAN | - |
| 23-24 | | Adrian Braun (F) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Francisco DeLuca (F) | - | | - |
| 23-24 | | Cody Farrell (F) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Julian Fedora (F) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Kalan Glew (F) | - | | - |
| 23-24 | | Sam Grunewald (F) | 2009 | | - |
| 23-24 | | Noah Madison (F) | 2008 | MB, CAN | - |
| 23-24 | | Luke Marykuca (F) | 2007 | Winnipeg, MB, CAN | - |
| 23-24 | | Zach Mestdagh (F) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Tyson Nimetz (F) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Jack Ross (F) | 2008 | Winnipeg, MB, CAN | - |
| 23-24 | | Pierce Wells (F) | 2008 | | - |
| 23-24 | | Carter Polanski (F) | 2008 | MB, CAN | - |
| 22-23 | | Leyton Medwick (G) | 2006 | MB, CAN | - |
| 22-23 | | Taye Timmerman (G) | 2007 | Winnipeg, MB, CAN | - |
| 22-23 | | Baron Baker (D) | 2006 | MB, CAN | - |
| 22-23 | | Adam Blair (D) | 2008 | | - |
| 22-23 | | Kale Chipman (D) | 2006 | MB, CAN | - |
| 22-23 | | Danny Cross (D) | 2008 | Winnipeg, MB, CAN | - |
| 22-23 | | Parker Hyra (D) | 2007 | | - |
| 22-23 | | Matthew Sawchyn (D) | 2006 | | - |
| 22-23 | | Keegan Thorn (D) | 2007 | Winnipeg, MB, CAN | - |
| 22-23 | | Lukas Mager (F) | 2006 | MB, CAN | - |
| 22-23 | | Carson White (F) | 2006 | Winnipeg, MB, CAN | - |
| 22-23 | | Alexandre Andre (F) | 2008 | Winnipeg, MB, CAN | - |
| 22-23 | | Shea Chornley (F) | 2007 | Winnipeg, MB, CAN | - |
| 22-23 | | Antonio Cotroneo (F) | 2007 | | - |
| 22-23 | | Ben Dnes (F) | 2008 | MB, CAN | - |
| 22-23 | | Jaxson Fillion (F) | 2006 | MB, CAN | - |
| 22-23 | | Tyler Free (F) | 2007 | Winnipeg, MB, CAN | - |
| 22-23 | | Caden Gordon (F) | 2007 | | - |
| 22-23 | | Dylan Jaquet (F) | 2006 | MB, CAN | - |
| 22-23 | | Matthew O'Sullivan (F) | 2006 | Winnipeg, MB, CAN | - |
| 22-23 | | Tyriece Pattyn (F) | 2007 | MB, CAN | - |
| 22-23 | | Mikey Thomas (F) | 2007 | Winnipeg, MB, CAN | - |
| 22-23 | | Connor Vandal (F) | 2007 | Winnipeg, MB, CAN | - |
| 22-23 | | Brody Green (F) | 2007 | Winnipeg, MB, CAN | - |
| 21-22 | | Alex Domenico (G) | 2005 | MB, CAN | - |
| 21-22 | | Leyton Medwick (G) | 2006 | MB, CAN | - |
| 21-22 | | Baron Baker (D) | 2006 | MB, CAN | - |
| 21-22 | | Dylan Bauknecht (D) | 2005 | MB, CAN | - |
| 21-22 | | Lucas Boulanger (D) | 2007 | Winnipeg, MB, CAN | - |
| 21-22 | | Kale Chipman (D) | 2006 | MB, CAN | - |
| 21-22 | | Jacob Howell (D) | 2005 | | - |
| 21-22 | | Matthew Sawchyn (D) | 2006 | | - |
