Wins  | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 4 | 56 |  Aaron Lewadniuk (F) | 1989 | Carman, MB, CAN | - |
| 2 | 61 | Brenden Walker (F) | 1992 | Ste. Anne, MB, CAN | - |
| 2 | 59 | Mike Rey (F) | 1989 | Winnipeg, MB, CAN | - |
| 2 | 57 | Jon Froese (F) | 1982 | Winkler, MB, CAN | - |
| 2 | 54 | Ryan Dyck (F) | 1979 | Lowe Farm, MB, CAN | - |
| 2 | | Rob Hamm (F) | - | | - |
| 2 | | Greg Waldvogel (F) | - | | - |
| 2 | | Dale Rempel (F) | - | | - |
| 2 | | Brian Coates (F) | 1952 | Carman, MB, CAN | Boston Bruins (1972) |
| 2 | | Mike Kehler (F) | - | | - |
| 1 | 37 | Andrew Clark (D) | 1993 | Brandon, MB, CAN | - |
| 1 | 37 | Adam Hughesman (F) | 1991 | Winnipeg, MB, CAN | - |
| 1 | 42 | Matt Gingera (F) | 1987 | Winnipeg, MB, CAN | - |
| 1 | 45 | Eric Delong (F) | 1988 | Oakville, MB, CAN | - |
| 1 | 49 | Devon LeBlanc (F) | 1988 | Brandon, MB, CAN | - |
| 1 | 60 | Jay Fehr (F) | 1989 | Morden, MB, CAN | - |
| 1 | 54 | Keith Bially (F) | 1986 | MB, CAN | - |
| 1 | 48 | Jordan Hack (F) | 1983 | Stony Mountain, MB, CAN | - |
| 1 | 50 | Warren McCutcheon (F) | 1982 | Carman, MB, CAN | New Jersey Devils (2000) |
| 1 | 80 | Ryan Butterfield (F) | 1978 | Dugald, MB, CAN | - |
| 1 | 50 | Jeff McGill (F) | 1979 | Carman, MB, CAN | - |
| 1 | | Jeremy Matuszewski (F) | - | | - |
| 1 | | Dan Delorme (F) | - | | - |
| 1 | | Mike Krentz (F) | - | MB, CAN | - |
| 1 | | Kirk Feasey (F) | 1977 | MB, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 24-25 | 61 | Brenden Walker (F) | 1992 | Ste. Anne, MB, CAN | - |
| 23-24 | 48 | Brenden Walker (F) | 1992 | Ste. Anne, MB, CAN | - |
| 22-23 | 42 | Mike Rey (F) | 1989 | Winnipeg, MB, CAN | - |
| 21-22 | 37 | Andrew Clark (D) | 1993 | Brandon, MB, CAN | - |
| 21-22 | 37 | Adam Hughesman (F) | 1991 | Winnipeg, MB, CAN | - |
| 19-20 | 45 | Aaron Lewadniuk (F) | 1989 | Carman, MB, CAN | - |
| 18-19 | 59 | Mike Rey (F) | 1989 | Winnipeg, MB, CAN | - |
| 17-18 | 42 | Matt Gingera (F) | 1987 | Winnipeg, MB, CAN | - |
| 16-17 | 50 | Aaron Lewadniuk (F) | 1989 | Carman, MB, CAN | - |
| 15-16 | 56 | Aaron Lewadniuk (F) | 1989 | Carman, MB, CAN | - |
| 14-15 | 45 | Eric Delong (F) | 1988 | Oakville, MB, CAN | - |
| 13-14 | 49 | Devon LeBlanc (F) | 1988 | Brandon, MB, CAN | - |
| 12-13 | 45 | Aaron Lewadniuk (F) | 1989 | Carman, MB, CAN | - |
| 11-12 | 60 | Jay Fehr (F) | 1989 | Morden, MB, CAN | - |
| 10-11 | 54 | Keith Bially (F) | 1986 | MB, CAN | - |
| 09-10 | 48 | Jordan Hack (F) | 1983 | Stony Mountain, MB, CAN | - |
| 08-09 | 50 | Warren McCutcheon (F) | 1982 | Carman, MB, CAN | New Jersey Devils (2000) |
| 07-08 | 57 | Jon Froese (F) | 1982 | Winkler, MB, CAN | - |
| 06-07 | 54 | Ryan Dyck (F) | 1979 | Lowe Farm, MB, CAN | - |
| 05-06 | 80 | Ryan Butterfield (F) | 1978 | Dugald, MB, CAN | - |
| 04-05 | 44 | Jon Froese (F) | 1982 | Winkler, MB, CAN | - |
| 03-04 | 50 | Jeff McGill (F) | 1979 | Carman, MB, CAN | - |
| 02-03 | 44 | Ryan Dyck (F) | 1979 | Lowe Farm, MB, CAN | - |
| 01-02 | | Jeremy Matuszewski (F) | - | | - |
| 00-01 | | Dan Delorme (F) | - | | - |
| 99-00 | | Mike Krentz (F) | - | MB, CAN | - |
| 98-99 | | Kirk Feasey (F) | 1977 | MB, CAN | - |
| 97-98 | | Joe Caldwell (F) | 1972 | Fisher Branch, MB, CAN | - |
| 96-97 | | Pat Penner (F) | 1968 | Steinbach, MB, CAN | - |
| 95-96 | | Andy Williamson (F) | - | | - |
| 94-95 | | Rob Hamm (F) | - | | - |
| 93-94 | | Rob Hamm (F) | - | | - |
| 92-93 | | Jamie Hickes (F) | - | | - |
| 91-92 | 96 | Mike Martens (F) | 1968 | Morris, MB, CAN | - |
| 90-91 | | Greg Waldvogel (F) | - | | - |
| 89-90 | |  Scott Knudson (F) | - | | - |
| 88-89 | | Shane Moffatt (F) | 1962 | Souris, MB, CAN | - |
| 86-87 | | Greg Waldvogel (F) | - | | - |
| 85-86 | | Henry Derksen (F) | - | | - |
| 84-85 | | Dale Rempel (F) | - | | - |
| 83-84 | | Mike Kehler (F) | - | | - |
| 82-83 | | Dale Rempel (F) | - | | - |
| 81-82 | | Brian Coates (F) | 1952 | Carman, MB, CAN | Boston Bruins (1972) |
| 80-81 | | Brian Coates (F) | 1952 | Carman, MB, CAN | Boston Bruins (1972) |
| 79-80 | | Marlin Vanrobaeys (F) | 1955 | | - |
| 78-79 | | Mike Kehler (F) | - | | - |
| 77-78 | | Dave Martin (F) | - | | - |
