| 24-25 | |  Connor Paronuzzi (F) | 2005 | Emeryville, ON, CAN | - |
| 23-24 | | Trenton Penner (F) | 2003 | Winkler, MB, CAN | - |
| 22-23 | | Lucas Brennan (F) | 2004 | Winnipeg, MB, CAN | - |
| 21-22 | | Braden Fischer (F) | 2002 | Winnipeg, MB, CAN | - |
| 19-20 | | Grady Hobbs (F) | 2000 | Deloraine, MB, CAN | - |
| 18-19 | | Joshua Tripp (F) | 1998 | Swan River, MB, CAN | - |
| 17-18 | | Dexter Kuczek (F) | 1997 | East St. Paul, MB, CAN | - |
| 16-17 | | Brady Keeper (D) | 1996 | Cross Lake, MB, CAN | - |
| 15-16 | | Brad Bowles (F) | 1995 | Elkhorn, MB, CAN | - |
| 14-15 | | Tristan Keck (F) | 1995 | Morris, MB, CAN | - |
| 13-14 | | Parker Thomas (F) | 1993 | Winnipeg, MB, CAN | - |
| 12-13 | | Guillaume Naud (D) | 1992 | Augsburg, GER | - |
| 11-12 | | Jayson Argue (G) | 1993 | Swan River, MB, CAN | - |
| 10-11 | | Shane Luke (F) | 1990 | Saint Rose Du Lac, MB, CAN | - |
| 09-10 | | Taylor Dickin (F) | 1989 | Winnipeg, MB, CAN | - |
| 08-09 | | Eric Delong (F) | 1988 | Oakville, MB, CAN | - |
| 07-08 | | Bryan Kauk (F) | 1987 | Brandon, MB, CAN | - |
| 06-07 | | Brant Hilton (G) | 1986 | Winnipeg, MB, CAN | - |
| 05-06 | | Tyler Czuba (F) | 1985 | Kelowna, BC, CAN | - |
| 04-05 | | Ryan Garbutt (F) | 1985 | Winnipeg, MB, CAN | - |
| 03-04 | | Aaron Starr (F) | 1983 | Saskatoon, SK, CAN | - |
| 02-03 | | Tyler Skworchinski (F) | 1982 | Marathon, ON, CAN | - |
| 01-02 | | Marc-André Leclerc (G) | 1981 | Montréal, QC, CAN | - |
| 00-01 | | Lee Stubbs (F) | 1980 | Winnipeg, MB, CAN | - |
| 99-00 | | Junior Lessard (F) | 1980 | St-Joseph-de-Beauce, QC, CAN | - |
| 98-99 | | Jeff McGill (F) | 1979 | Carman, MB, CAN | - |
| 97-98 | | Jedd Crumb (F) | 1977 | Winnipeg, MB, CAN | - |
| 96-97 | | Chris Thomas (F) | 1976 | MB, CAN | - |
| 95-96 | | Paul Carey (F) | 1975 | Winnipeg, MB, CAN | - |
| 94-95 | | Cory Cyrenne (F) | 1977 | Winnipeg, MB, CAN | San Jose Sharks (1996) |
| 93-94 | | Ryan Smith (F) | 1973 | Winnipeg, MB, CAN | - |
| 92-93 | | Dane Litke (D) | 1972 | Beausejour, MB, CAN | - |
| 91-92 | | Derek Picklyk (F) | 1971 | St. James, MB, CAN | - |
| 90-91 | | Jeff Tomlinson (F) | 1970 | Winnipeg, MB, CAN | - |
| 89-90 | | Reg Spence (F) | 1970 | | - |
| 88-89 | | Paul Thompson (D) | 1968 | Thompson, MB, CAN | New York Islanders (1986) |
| 87-88 | | Brad McGinnis (F) | 1969 | Saskatoon, SK, CAN | - |
| 86-87 | | Paul Harland (F) | - | Portage la Prairie, MB, CAN | - |
| 85-86 | | Steve Harder (F) | 1965 | Winkler, MB, CAN | - |
| 84-85 | | Brian Thomson (F) | 1964 | Miami, MB, CAN | - |
| 83-84 | | Mike Vinsky (F) | 1964 | Winnipeg, MB, CAN | - |
| 82-83 | | Mike Ridley (F) | 1963 | Winnipeg, MB, CAN | - |
| 81-82 | | Grant Ledyard (D) | 1961 | Winnipeg, MB, CAN | - |
| 80-81 | | Darren Boyko (F) | 1964 | Winnipeg, MB, CAN | - |
| 79-80 | | Brad Lamb (G) | - | | - |
| 78-79 | |  Karl Friesen (G) | 1958 | Winnipeg, MB, CAN | - |
| 77-78 | | Ken Krentz (F) | 1957 | Steinbach, MB, CAN | - |
| 76-77 | | Jim Misener (F) | 1956 | Roblin, MB, CAN | - |
| 75-76 | | Darrell Einarson (D) | 1957 | Morden, MB, CAN | - |
| 74-75 | | James Cruise (F) | 1955 | Dauphin, MB, CAN | - |
| 73-74 | | Mark Izzard (F) | 1954 | Winnipeg, MB, CAN | - |
| 72-73 | | Brian Engblom (D) | 1955 | Winnipeg, MB, CAN | Montréal Canadiens (1975) |
| 65-66 | | Terry Jones (F) | 1946 | Winnipeg, MB, CAN | New York Rangers (1963) |
| 64-65 | | Wayne Stephenson (G) | 1945 | Fort William, ON, CAN | - |
| 59-60 | | George Hill (F) | 1941 | Winnipeg, MB, CAN | - |
| 57-58 | | Gord Labossiere (F) | 1940 | St. Boniface, MB, CAN | - |
| 56-57 | | Ray Brunel (F) | 1936 | St. Lucipin, MB, CAN | - |
