Named after the DFHL's first and only Trades Commissioner, the Al Ashley Trophy is awarded to the playoff champion of the Gordie Howe Conference.
| Season | Winner(s) |
|---|---|
| 38 | Boston Bruins (GM: Cory Jordan) |
| 37 | Detroit Red Wings (GM: Brian Stewart) |
| 36 | Hamilton Tigers (GM: Dan Marvin) |
| 35 | Detroit Red Wings (GM: Brian Stewart) |
| 34 | Hamilton Tigers (GM: Dan Marvin) |
| 33 | Hamilton Tigers (GM: Dan Marvin) |
| 32 | Toronto Maple Leafs (GM: Mark Coleman) |
| 31 | Detroit Red Wings (GM: Brian Stewart) |
| 30 | New York Americans (GM: Neil Burke) |
| 29 | Chicago Black Hawks (GM: Chris Barnett) |
| 28 | Hamilton Tigers (GM: Dan Marvin) |
| 27 | Chicago Black Hawks (GM: Chris Barnett) |
| 26 | Detroit Red Wings (GM: Brian Stewart) |
| 25 | Hamilton Tigers (GM: Dan Marvin) |
| 24 | Hamilton Tigers (GM: Dan Marvin) |
| 23 | Detroit Red Wings (GM: Brian Stewart) |
| 22 | Montreal Canadiens (GM: Joey Loonen) |
| 21 | New York Americans (GM: Neil Burke) |
| 20 | New York Americans (GM: Neil Burke) |
| 19 | New York Americans (GM: Neil Burke) |
| 18 | Hamilton Tigers (GM: Dan Marvin) |
| 17 | Montreal Canadiens (GM: Joey Loonen) |
| 16 | Montreal Canadiens (GM: Joey Loonen) |
| 15 | Hamilton Tigers (GM: Dan Marvin) |
| 14 | New York Americans (GM: Neil Burke) |
| 13 | Boston Bruins (GM: Mike Brinton) |
| 12 | Hamilton Tigers (GM: Dan Marvin) |
| 11 | Chicago Black Hawks (GM: Chris Clement) |
| 10 | New York Rangers (GM: Shawn Guest) |
| 9 | Toronto Maple Leafs (GM: Steve Moore) |
| 8 | Detroit Red Wings (GM: Brian Stewart) |
| 7 | Montreal Canadiens (GM: Joey Loonen) |
| 6 | Boston Bruins (GM: Mike Brinton) |
| 5 | Boston Bruins (GM: Mike Brinton) |
| 4 | Pittsburgh Pirates (GM: Larry Marhofer) |
| 3 | Boston Bruins (GM: Jeff G.) |
| 2 | Detroit Red Wings (GM: Al Ashley) |
| 1 | New York Rangers (GM: Dave Taylor) |