Biggest trades Toronto Maple Leafs

Toronto Maple Leafs acquire	Date	Colorado Avalanche acquire
Tyson Barrie Alex Kerfoot 2020 6th round pick	July 1, 2019	Nazem Kadri Calle Rosen 2020 3rd round pick

Pittsburgh Penguins acquire	Date	Toronto Maple Leafs acquire
Phil Kessel Tim Erixon Tyler Biggs 2016 conditional 2nd round pick	July 1, 2015	Kasperi Kapanen Scott Harrington Nick Spaling 2016 conditional 1st round pick 2016 3rd round pick

Toronto Maple Leafs acquire	Date	Quebec Nordiques acquire
Garth Butcher Mats Sundin Todd Warriner 1994 1st round pick (#10-Nolan Baumgartner)	June 28, 1994	Wendel Clark Sylvain Lefebvre Landon Wilson 1994 1st round pick (#22-Jeff Kealty)

Toronto Maple Leafs acquire	Date	Calgary Flames acquire
Doug Gilmour Jamie Macoun Kent Manderville Ric Nattress Rick Wamsley	January 2, 1992	Craig Berube Alexander Godynyuk Gary Leeman Michel Petit Jeff Reese

Toronto Maple Leafs acquire	Date	Detroit Red Wings acquire
Norm Ullman Floyd Smith Paul Henderson Doug Barrie	March 3, 1968	Garry Unger Pete Stemkowski Frank Mahovlich rights to Carl Brewer

Toronto Maple Leafs acquire	Date	Chicago Blackhawks acquire
Max Bentley Cy Thomas	November 2, 1947	Gus Bodnar Ernie Dickens Bob Goldham Bud Poile Gaye Stewart