| Date | Details |
|---|---|
| February 25, 2020 | Toronto Maple Leafs relenquish the rights to three players: |
| September 15, 2019 | Matt Cullen claimed by Toronto Maple Leafs from Boston Bruins |
| October 5, 2015 | Boston Bruins and New York Rangers swap teams |
| July 26, 2009 | To New York Rangers:To Toronto Maple Leafs:
|
| June 10, 2009 | To Colorado Rockies:To Toronto Maple Leafs: |
| September 24, 2005 | Colorado Rockies and Montreal Maroons swap teams |
| October 26, 2003 | To Detroit Red Wings:
To Montreal Maroons:
|
| October 14, 2003 | To Detroit Red Wings:
To Pittsburgh Pirates: |
| March 23, 2002 | |
| January 15, 2001 | Drafted by Boston Bruins, dFHL Inaugural Draft (Round 1, 41st Overall) |