| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 5 | |  Dustin Cooney (D) | - | | - |
| 5 | | Drew Istace (F) | 1983 | Pilot Butte, SK, CAN | - |
| 5 | | Cory Unser (D) | 1980 | Sedley, SK, CAN | - |
| 4 | | Lance Herauf (F) | 1984 | Balgonie, SK, CAN | - |
| 4 | | Grant Selinger (F) | 1983 | Regina, SK, CAN | - |
| 3 | | Brad Reaney (F) | 1986 | Ceylon, SK, CAN | - |
| 3 | | Jason Vermeulen (F) | 1980 | Ceylon, SK, CAN | - |
| 3 | | Kyle Kapell (F) | 1988 | | - |
| 3 | | Chad Richardson (F) | 1984 | Regina, SK, CAN | - |
| 3 | | Kurtis Selinger (D) | - | | - |
| 3 | | Jason Weitzel (F) | 1980 | Balgonie, SK, CAN | - |
| 3 | | Randy Weinberger (G) | - | Regina, SK, CAN | - |
| 3 | | Terrance Marion (F) | - | | - |
| 2 | | Kale Haylock (F) | 1991 | Grenfell, SK, CAN | - |
| 2 | | Justin Hollinger (D) | 1990 | Neudorf, SK, CAN | - |
| 2 | | Daniel Hope (F) | 1988 | Kelvington, SK, CAN | - |
| 2 | | Craig Karius (D) | 1990 | Melville, SK, CAN | - |
| 2 | | Allan Killback (F) | 1994 | Emerald Park, SK, CAN | - |
| 2 | | Sanfred King (F) | 1990 | Brandon, MB, CAN | - |
| 2 | | Brayden Metz (F) | 1990 | Regina, SK, CAN | - |
| 2 | | Skyler Reeve (D) | 1996 | Grenfell, SK, CAN | - |
| 2 | | T.J. Reeve (F) | 1994 | Grenfell, SK, CAN | - |
| 2 | | Braden Reiger (D) | 1985 | Grenfell, SK, CAN | - |
| 2 | | Michael Rogoschewsky (F) | 1990 | Melville, SK, CAN | - |
| 2 | | Colton Schick (F) | 1994 | Neudorf, SK, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 18-19 | | Riley Ross (G) | 1989 | Kronau, SK, CAN | - |
| 18-19 | | Thomas Spence (G) | 1996 | Moose Jaw, SK, CAN | - |
| 18-19 | | Austin Bourhis (D) | 1992 | Kipling, SK, CAN | - |
| 18-19 | | Austin Brown (D) | 1995 | Mississauga, ON, CAN | - |
| 18-19 | | Jacob Cardiff (D) | 1996 | Regina, SK, CAN | - |
| 18-19 | | Jake Coulter (D) | 1997 | Hamiota, MB, CAN | - |
| 18-19 | | Dryden Isley (D) | - | | - |
| 18-19 | | Johnathon Sonntag (D) | 1990 | Meadow Lake, SK, CAN | - |
| 18-19 | | Lucas Stubel (D) | 1990 | Estevan, SK, CAN | - |
| 18-19 | | Tanner Vandesype (D) | 1988 | Weyburn, SK, CAN | - |
| 18-19 | | Chance Olsen (D) | 1984 | Moose Jaw, SK, CAN | - |
| 18-19 | | Cam McGeough (F) | 1988 | Regina, SK, CAN | - |
| 18-19 | | Brad Reaney (F) | 1986 | Ceylon, SK, CAN | - |
| 18-19 | | Kaelum Bieber (F) | 1994 | Midale, SK, CAN | - |
| 18-19 | | KC Brooks (F) | - | Gray, SK, CAN | - |
| 18-19 | | Morgan Gallais (F) | 1996 | Regina, SK, CAN | - |
| 18-19 | | Dyllon Giblett (F) | 1991 | Estevan, SK, CAN | - |
| 18-19 | | Brandon Halbgewachs (F) | 1994 | White City, SK, CAN | - |
| 18-19 | | Cody Hegion (F) | 1996 | Regina, SK, CAN | - |
| 18-19 | | Paul Sonntag (F) | 1992 | Goodsoil, SK, CAN | - |
| 18-19 | | Ian Williams (F) | 1995 | Gray, SK, CAN | - |
| 18-19 | | Shane Cole (F) | - | | - |
| 18-19 | | Logan Gorsalitz (F) | 1986 | Fort McMurray, AB, CAN | - |
| 17-18 | | Mitch Kilgore (G) | 1991 | Outlook, SK, CAN | - |
| 17-18 | | Justin Hollinger (D) | 1990 | Neudorf, SK, CAN | - |
| 17-18 | | Craig Karius (D) | 1990 | Melville, SK, CAN | - |
| 17-18 | | Skyler Reeve (D) | 1996 | Grenfell, SK, CAN | - |
| 17-18 | | Mark Schneider (D) | 1990 | Brandon, MB, CAN | - |
| 17-18 | | Braden Reiger (D) | 1985 | Grenfell, SK, CAN | - |
| 17-18 | | Nathan Boyer (F) | 1992 | Prince Albert, SK, CAN | - |
| 17-18 | | Allan Killback (F) | 1994 | Emerald Park, SK, CAN | - |
| 17-18 | | Brayden Metz (F) | 1990 | Regina, SK, CAN | - |
| 17-18 | | Kale Haylock (F) | 1991 | Grenfell, SK, CAN | - |
| 17-18 | | Michael Rogoschewsky (F) | 1990 | Melville, SK, CAN | - |
| 17-18 | | Lane Harbor (F) | 1994 | Val Marie, SK, CAN | - |
| 17-18 | | Daniel Hope (F) | 1988 | Kelvington, SK, CAN | - |
| 17-18 | | Sanfred King (F) | 1990 | Brandon, MB, CAN | - |
| 17-18 | | T.J. Reeve (F) | 1994 | Grenfell, SK, CAN | - |
| 17-18 | | Colton Schick (F) | 1994 | Neudorf, SK, CAN | - |
| 17-18 | | Daniel Wanner (F) | 1995 | Estevan, SK, CAN | - |
| 16-17 | | Joshua Switzer (G) | 1993 | Grenfell, SK, CAN | - |
| 16-17 | | Tyler Bird (D) | 1992 | Regina, SK, CAN | - |
| 16-17 | | Justin Hollinger (D) | 1990 | Neudorf, SK, CAN | - |
| 16-17 | | Craig Karius (D) | 1990 | Melville, SK, CAN | - |
| 16-17 | | Tyler Krauser (D) | - | | - |
| 16-17 | | Skyler Reeve (D) | 1996 | Grenfell, SK, CAN | - |
| 16-17 | | Mark Schneider (D) | 1990 | Brandon, MB, CAN | - |
| 16-17 | | Braden Reiger (D) | 1985 | Grenfell, SK, CAN | - |
| 16-17 | | Dylan Kent (F) | 1991 | Grenfell, SK, CAN | - |
| 16-17 | | Allan Killback (F) | 1994 | Emerald Park, SK, CAN | - |
| 16-17 | | Brayden Metz (F) | 1990 | Regina, SK, CAN | - |
| 16-17 | | Kale Haylock (F) | 1991 | Grenfell, SK, CAN | - |
| 16-17 | | Michael Rogoschewsky (F) | 1990 | Melville, SK, CAN | - |
| 16-17 | | Nolan Souchotte (F) | 1990 | Wolseley, SK, CAN | - |
| 16-17 | | Daniel Hope (F) | 1988 | Kelvington, SK, CAN | - |
| 16-17 | | Sanfred King (F) | 1990 | Brandon, MB, CAN | - |
| 16-17 | | Colin Mospanchuk (F) | 1993 | Winnipeg, MB, CAN | - |
| 16-17 | | T.J. Reeve (F) | 1994 | Grenfell, SK, CAN | - |
| 16-17 | | Colton Schick (F) | 1994 | Neudorf, SK, CAN | - |
| 16-17 | | Daniel Wanner (F) | 1995 | Estevan, SK, CAN | - |
| 15-16 | | Nathan Bailey (G) | - | | - |
| 15-16 | | Kale Thomson (G) | 1993 | Yorkton, SK, CAN | - |
| 15-16 | | Denin Bosch (D) | 1993 | SK, CAN | - |
| 15-16 | | Dustin Cooney (D) | - | | - |
| 15-16 | | Jens Johnson (D) | 1992 | Regina, SK, CAN | - |
| 15-16 | | Mitch Peeke (D) | 1989 | Raymore, SK, CAN | - |
| 15-16 | | Eric Macoretta (D) | 1993 | Balgonie, SK, CAN | - |
| 15-16 | | Logan Herauf (F) | 1990 | Balgonie, SK, CAN | - |
| 15-16 | | Logan Herchak (F) | 1995 | Regina, SK, CAN | - |
| 15-16 | | Drew Istace (F) | 1983 | Pilot Butte, SK, CAN | - |
| 15-16 | | Matt Coupal (F) | 1994 | Emerald Park, SK, CAN | - |
| 15-16 | | Jaret Eberle (F) | - | | - |
| 15-16 | | Zach Cardiff (F) | 1993 | Wilcox, SK, CAN | - |
| 15-16 | | Brady Anderson (F) | 1993 | Regina, SK, CAN | - |
| 15-16 | | Davis Firlotte (F) | 1993 | White City, SK, CAN | - |
| 15-16 | | Lance Herauf (F) | 1984 | Balgonie, SK, CAN | - |
| 15-16 | | Nathan Murray (F) | 1992 | Regina, SK, CAN | - |
| 15-16 | | Riley Nargang (F) | 1992 | Edenwold, SK, CAN | - |
| 15-16 | | Tyler Stewart (F) | 1985 | Regina, SK, CAN | - |
| 14-15 | | Blake DeBruyne (G) | - | | - |
| 14-15 | | Landon Irwin (G) | - | | - |
| 14-15 | | Cody Cossar (D) | 1988 | Weyburn, SK, CAN | - |
| 14-15 | | Mitchell Ferguson (D) | - | | - |
| 14-15 | | Mike Floer (D) | - | | - |
| 14-15 | | Grant Jensen (D) | 1992 | Radville, SK, CAN | - |
| 14-15 | | Jesse Niemigeers (D) | - | | - |
| 14-15 | | Reid Paterson (D) | - | | - |
| 14-15 | | Wade van de Sype (D) | - | | - |
| 14-15 | | Taylor Vandesype (D) | 1991 | Assiniboia, SK, CAN | - |
| 14-15 | | Rylan Kaip (F) | 1984 | Wilcox, SK, CAN | Atlanta Thrashers (2003) |
| 14-15 | | Brad Reaney (F) | 1986 | Ceylon, SK, CAN | - |
| 14-15 | | Torrey Lindsay (F) | 1988 | Grosse Isle, MB, CAN | - |
| 14-15 | | Adam McEwen (F) | - | | - |
| 14-15 | | Casey Pirio (F) | 1993 | Radville, SK, CAN | - |
| 14-15 | | Brett Tuchscherer (F) | - | | - |
| 14-15 | | Jason Vermeulen (F) | 1980 | Ceylon, SK, CAN | - |
| 14-15 | | Brendon Vertefeuille (F) | 1986 | Weyburn, SK, CAN | - |
| 14-15 | | Matt Bourassa (F) | 1992 | Regina, SK, CAN | - |
| 14-15 | | Eric Calibaba (F) | 1988 | Radville, SK, CAN | - |
| 14-15 | | Corey Koski (F) | 1981 | Weyburn, SK, CAN | - |
