| 24-25 | |  Mitchell Kathler (G) | 2006 | Airdrie, AB, CAN | - |
| 23-24 | | Grady Hoffman (F) | 2005 | Yorkton, SK, CAN | - |
| 22-23 | | Carter Cormier (F) | 2004 | Kindersley, SK, CAN | - |
| 21-22 | | Carson Buydens (F) | 2004 | Gladstone, MB, CAN | - |
| 19-20 | | Carter Loney (F) | 2002 | Columbus, OH, USA | - |
| 18-19 | | Owen Murray (D) | 2002 | Decker, MB, CAN | - |
| 17-18 | | Justin Lee (D) | 2000 | Waskada, MB, CAN | - |
| 16-17 | |  Cole Weaver (G) | 1998 | Champlin, MN, USA | - |
| 15-16 | | Nick Henry (F) | 1999 | Portage la Prairie, MB, CAN | Colorado Avalanche (2017) |
| 14-15 | | James Shearer (D) | 1997 | Brandon, MB, CAN | - |
| 13-14 | | Tyler Jeanson (F) | 1997 | Carman, MB, CAN | - |
| 12-13 | | Tristan Keck (F) | 1995 | Morris, MB, CAN | - |
| 11-12 | | Tanner Jago (D) | 1994 | Brandon, MB, CAN | - |
| 10-11 | | Bryn Chyzyk (F) | 1992 | Virden, MB, CAN | - |
| 09-10 | | Brendan O'Donnell (F) | 1992 | Winnipeg, MB, CAN | Tampa Bay Lightning (2010) |
| 08-09 | | Jordan DePape (F) | 1992 | Winnipeg, MB, CAN | - |
| 07-08 | | Stephan Vigier (F) | 1990 | Notre-Dame-de-Lourdes, MB, CAN | - |
| 06-07 | | Aaron Lewadniuk (F) | 1989 | Carman, MB, CAN | - |
| 05-06 | | Jason Gregoire (F) | 1989 | Winnipeg, MB, CAN | New York Islanders (2007) |
| 04-05 | | Matt Ostash (F) | 1985 | Brandon, MB, CAN | - |
| 03-04 | | Mark Magnowski (F) | 1986 | Winnipeg, MB, CAN | - |
| 02-03 | | Andrew Jackman (F) | 1984 | Winnipeg, MB, CAN | - |
| 01-02 | | Blaine Jarvis (F) | 1984 | Gladstone, MB, CAN | - |
| 00-01 | | Mark Agnew (F) | 1983 | Hartney, MB, CAN | - |
| 99-00 | | D.J Huver (G) | 1982 | Winnipeg, MB, CAN | - |
| 98-99 | | Myles Kuharski (F) | 1981 | Neepawa, MB, CAN | - |
| 97-98 | | Andrew Kirk (F) | - | MB, CAN | - |
| 96-97 | | Tyler Arnason (F) | 1979 | Oklahoma City, OK, USA | Chicago Blackhawks (1998) |
| 95-96 | | David Burgess (F) | 1977 | Crystal City, MB, CAN | - |
| 94-95 | | Derek Robertson (F) | 1976 | Thunder Bay, ON, CAN | - |
| 93-94 | | Cory Cyrenne (F) | 1977 | Winnipeg, MB, CAN | San Jose Sharks (1996) |
| 92-93 | | Ken Donaldson (F) | 1975 | Dauphin, MB, CAN | - |
| 91-92 | | Ryan Smith (F) | 1973 | Winnipeg, MB, CAN | - |
| 90-91 | | Brent McMillan (F) | 1972 | Thompson, MB, CAN | - |
| 89-90 | | Geoff Bumstead (F) | 1972 | Winnipeg, MB, CAN | - |
| 88-89 | | Kevin Moore (F) | 1971 | Winnipeg, MB, CAN | - |
| 88-89 | | Keith Morris (F) | 1971 | Winnipeg, MB, CAN | Winnipeg Jets (1990) |
| 87-88 | | Russ Romaniuk (F) | 1970 | Winnipeg, MB, CAN | Winnipeg Jets (1988) |
| 86-87 | | Myles Hubbard (F) | 1968 | Shellbrook, SK, CAN | - |
| 85-86 | | Neil Wilkinson (D) | 1967 | Selkirk, MB, CAN | Minnesota North Stars (1986) |
| 84-85 | | Russ Parent (D) | 1968 | Winnipeg, MB, CAN | New York Rangers (1986) |
| 83-84 | | Glenn Revak (F) | 1966 | Winnipeg, MB, CAN | - |
| 83-84 | | Brian Foreman (F) | 1966 | Winnipeg, MB, CAN | - |
| 82-83 | | Shane Eirickson (D) | 1965 | Lundar, MB, CAN | - |
| 81-82 | | Steve Harder (F) | 1965 | Winkler, MB, CAN | - |
| 80-81 | | Darren Boyko (F) | 1964 | Winnipeg, MB, CAN | - |
| 79-80 | | Bruce Eakin (F) | 1962 | Winnipeg, MB, CAN | Calgary Flames (1981) |
| 78-79 | | Mike Mahood (F) | - | | - |
| 77-78 | | Larry Beck (F) | - | Fort Frances, ON, CAN | - |
| 76-77 | | Bruno Rogger (D) | 1959 | Quesnel, BC, CAN | - |
| 75-76 | | Anthony Gurniak (F) | - | | - |
| 74-75 | | Ken Krentz (F) | 1957 | Steinbach, MB, CAN | - |
| 70-71 | | Bill Kriski (G) | 1954 | Winnipeg, MB, CAN | New York Rangers (1974) |
| 69-70 | | Frank Turnbull (G) | 1954 | Winnipeg, MB, CAN | - |
| 68-69 | | Jim Cahoon (F) | 1951 | Melville, SK, CAN | Montréal Canadiens (1971) |
| 67-68 | | Wayne Chernecki (F) | 1949 | Winnipeg, MB, CAN | Detroit Red Wings (1969) |
| 66-67 | | Bobby Clarke (F) | 1949 | Flin Flon, MB, CAN | Philadelphia Flyers (1969) |
| 65-66 | | Chuck Lefley (F) | 1950 | Winnipeg, MB, CAN | Montréal Canadiens (1970) |
| 64-65 | | Bill Ramsay (D) | - | Winnipeg, MB, CAN | Boston Bruins (1965) |
| 59-60 | | George Hill (F) | 1941 | Winnipeg, MB, CAN | - |
