Wins  | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 5 | |  Rob Hamm (F) | - | | - |
| 4 | | Steve Clark (F) | 1987 | | - |
| 4 | | Wayne Giesbrecht (F) | - | | - |
| 4 | | Mike Kehler (F) | - | | - |
| 2 | | Aaron Goldade (F) | 1980 | Prince Albert, SK, CAN | Buffalo Sabres (1998) |
| 2 | | Paul Gaudet (F) | 1982 | Winnipeg, MB, CAN | - |
| 1 | | Keith Grondin (F) | 1990 | Winnipeg, MB, CAN | - |
| 1 | | Mitch Doell (F) | 1993 | Winkler, MB, CAN | - |
| 1 | | Remi Laurencelle (F) | 1995 | Winnipeg, MB, CAN | - |
| 1 | | Michael St. Croix (F) | 1993 | Winnipeg, MB, CAN | New York Rangers (2011) |
| 1 | | Cody Friesen (F) | - | Winkler, MB, CAN | - |
| 1 | | Angus Klassen (F) | 1990 | Rosenort, MB, CAN | - |
| 1 | | Matthew Varnes (F) | 1989 | Winnipeg, MB, CAN | - |
| 1 | | Jay Fehr (F) | 1989 | Morden, MB, CAN | - |
| 1 | | Josh Froese (F) | 1985 | Winkler, MB, CAN | - |
| 1 | | Ramsay Fehr (F) | 1987 | Morden, MB, CAN | - |
| 1 | | Jay Roberts (F) | - | | - |
| 1 | | Chad Wrixon (F) | 1983 | Oak Bluff, MB, CAN | - |
| 1 | | Dan Delorme (F) | - | | - |
| 1 | | Ron Klassen (F) | - | | - |
| 1 | | Tyson Addison (F) | - | MB, CAN | - |
| 1 | | Jamie Hickes (F) | - | | - |
| 1 | | Derek Picklyk (F) | 1971 | St. James, MB, CAN | - |
| 1 | | Rob Smith (F) | 1971 | Baldur, MB, CAN | - |
| 1 | | Larry Maykut (F) | - | | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 23-24 | | Keith Grondin (F) | 1990 | Winnipeg, MB, CAN | - |
| 22-23 | | Mitch Doell (F) | 1993 | Winkler, MB, CAN | - |
| 21-22 | | Remi Laurencelle (F) | 1995 | Winnipeg, MB, CAN | - |
| 19-20 | | Michael St. Croix (F) | 1993 | Winnipeg, MB, CAN | New York Rangers (2011) |
| 18-19 | | Steve Clark (F) | 1987 | | - |
| 17-18 | | Cody Friesen (F) | - | Winkler, MB, CAN | - |
| 16-17 | | Steve Clark (F) | 1987 | | - |
| 15-16 | | Steve Clark (F) | 1987 | | - |
| 14-15 | | Angus Klassen (F) | 1990 | Rosenort, MB, CAN | - |
| 13-14 | | Matthew Varnes (F) | 1989 | Winnipeg, MB, CAN | - |
| 12-13 | | Steve Clark (F) | 1987 | | - |
| 11-12 | | Jay Fehr (F) | 1989 | Morden, MB, CAN | - |
| 10-11 | | Josh Froese (F) | 1985 | Winkler, MB, CAN | - |
| 09-10 | | Ramsay Fehr (F) | 1987 | Morden, MB, CAN | - |
| 08-09 | | Aaron Goldade (F) | 1980 | Prince Albert, SK, CAN | Buffalo Sabres (1998) |
| 07-08 | | Aaron Goldade (F) | 1980 | Prince Albert, SK, CAN | Buffalo Sabres (1998) |
| 06-07 | | Jay Roberts (F) | - | | - |
| 05-06 | | Paul Gaudet (F) | 1982 | Winnipeg, MB, CAN | - |
| 05-06 | | Chad Wrixon (F) | 1983 | Oak Bluff, MB, CAN | - |
| 04-05 | | Paul Gaudet (F) | 1982 | Winnipeg, MB, CAN | - |
| 03-04 | | Dan Delorme (F) | - | | - |
| 02-03 | | Ron Klassen (F) | - | | - |
| 01-02 | | Rob Hamm (F) | - | | - |
| 00-01 | | Tyson Addison (F) | - | MB, CAN | - |
| 99-00 | | Rob Hamm (F) | - | | - |
| 98-99 | | Jamie Hickes (F) | - | | - |
| 97-98 | | Rob Hamm (F) | - | | - |
| 96-97 | | Derek Picklyk (F) | 1971 | St. James, MB, CAN | - |
| 95-96 | | Rob Smith (F) | 1971 | Baldur, MB, CAN | - |
| 94-95 | | Larry Maykut (F) | - | | - |
| 93-94 | | Rob Hamm (F) | - | | - |
| 92-93 | | Quentin Doll (F) | - | | - |
| 88-89 | | Rob Hamm (F) | - | | - |
| 86-87 | | Wayne Giesbrecht (F) | - | | - |
| 85-86 | | Pat Owen (F) | - | | - |
| 84-85 | | Bob Toews (F) | - | | - |
| 83-84 | | Bill Whitehead (F) | - | | - |
| 82-83 | | Wayne Giesbrecht (F) | - | | - |
| 81-82 | | Mike Kehler (F) | - | | - |
| 80-81 | | Wayne Giesbrecht (F) | - | | - |
| 79-80 | | Wayne Giesbrecht (F) | - | | - |
| 79-80 | | Mike Kehler (F) | - | | - |
| 78-79 | | Mike Kehler (F) | - | | - |
| 77-78 | | Mike Kehler (F) | - | | - |
