Notable deals - Toronto Maple Leafs
| Pittsburgh Penguins acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
 | Phil Kessel | July 1, 2015 | Kasperi Kapanen |  |
| Tim Erixon | Scott Harrington | |||
| Tyler Biggs | Nick Spaling | |||
| 2016 conditional 2nd round pick | 2016 conditional 1st round pick | |||
| 2016 3rd round pick | ||||
| Columbus Blue Jackets acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
 | David Clarkson | February 26, 2015 | Nathan Horton | |
| Nashville Predators acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
 | Cody Franson | February 15, 2015 | Olli Jokinen | |
| Mike Santorelli | Brendan Leipsic | |||
| 2015 1st round pick | ||||
| Toronto Maple Leafs acquire | Date | St. Louis Blues acquire | ||
|---|---|---|---|---|
| Roman Polak | June 28, 2014 | 2014 4th round pick |  |
| Carl Gunnarsson | ||||
| Toronto Maple Leafs acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Dave Bolland | June 30, 2013 | 2013 2nd round pick (#51-Carl Dahlstrom) |  |
| 2013 4th round pick (#117-Fredrik Bergvik) | ||||
| 2014 4th round pick | ||||
| Toronto Maple Leafs acquire | Date | Los Angeles Kings acquire | ||
|---|---|---|---|---|
| Jonathan Bernier | June 23, 2013 | 2014 or 2015 2nd round pick |  |
| Ben Scrivens | ||||
| Matt Frattin | ||||
| cash | ||||
| Toronto Maple Leafs acquire | Date | Philadelphia Flyers acquire | ||
|---|---|---|---|---|
| James Van Riemsdyk | June 23, 2012 | Luke Schenn |  |
| Toronto Maple Leafs acquire | Date | Calgary Flames acquire | ||
|---|---|---|---|---|
| Keith Aulie | January 31, 2010 | Niklas Hagman |  |
| Dion Phaneuf | Jamal Mayers | |||
| Fredrik Sjostrom | Matt Stajan | |||
| Ian White | ||||
| Toronto Maple Leafs acquire | Date | Boston Bruins acquire | ||
|---|---|---|---|---|
| Phil Kessel | September 18, 2009 | 2010 1st round pick (#2-Tyler Seguin) |  |
| 2010 2nd round pick (#32-Jared Knight) | ||||
| 2011 1st round pick (#9-Dougie Hamilton) | ||||
| Toronto Maple Leafs acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Brian Leetch | March 3, 2004 | Jarkko Immonen |  |
| conditional draft pick (2004 #113-Roman Kukumberg) | Maxim Kondratiev | |||
| 2004 1st round pick (#24-Kris Chucko) | ||||
| 2005 2nd round pick (#40-Michael Sauer) | ||||
| Toronto Maple Leafs acquire | Date | San Jose Sharks acquire | ||
|---|---|---|---|---|
| Owen Nolan | March 5, 2003 | Brad Boyes |  |
| Alyn McCauley | ||||
| 2003 1st round pick (#21-Mark Stuart) | ||||
| Toronto Maple Leafs acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Bryan McCabe | October 2, 2000 | Alexander Karpovtsev | |
| 2001 4th round pick (#115-Vladimir Gusev) | ||||
| New Jersey Devils acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
 | Dave Ellett | February 25, 1997 | Jason Smith | |
| Doug Gilmour | Steve Sullivan | |||
| 1998 4th round pick or 1999 3rd round pick (1999 #95-Andre Lakos) | rights to Alyn McCauley | |||
| Toronto Maple Leafs acquire | Date | Dallas Stars acquire | ||
|---|---|---|---|---|
| Dave Gagner | January 28, 1996 | Benoit Hogue |  |
| 1996 6th round pick (#140-Dimitriy Yakushin) | Randy Wood | |||
| Toronto Maple Leafs acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Mike Gartner | March 21, 1994 | Glenn Anderson | |
| 1994 4th round pick (#100-Alexander Korobolin) | ||||
| rights to Scott Malone | ||||
| Toronto Maple Leafs acquire | Date | Edmonton Oilers acquire | ||
|---|---|---|---|---|
| Glenn Anderson | September 19, 1991 | Vincent Damphousse |  |
| Craig Berube | Peter Ing | |||
| Grant Fuhr | Luke Richardson | |||
| Scott Thornton | ||||
| cash | ||||
| future considerations | ||||
| Toronto Maple Leafs acquire | Date | Washington Capitals acquire | ||
|---|---|---|---|---|
| Bob Rouse | January 16, 1991 | Al Iafrate |  |
| Peter Zezel | ||||
| Toronto Maple Leafs acquire | Date | Winnipeg Jets acquire | ||
|---|---|---|---|---|
| Dave Ellett | November 10, 1990 | Ed Olczyk |  |
| Paul Fenton | Mark Osborne | |||
| Toronto Maple Leafs acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Ed Olczyk | September 3, 1987 | Bob McGill | |
| Al Secord | Steve Thomas | |||
| Rick Vaive | ||||
| Toronto Maple Leafs acquire | Date | Washington Capitals acquire | ||
|---|---|---|---|---|
| Mike Palmateer | September 9, 1982 | cash | |