Despite their contentious, competitive history, Toronto and Montréal have occasionally used each other to bolster their rosters by way of trades. While some franchises (such as Montréal and Boston) refuse to do business with each other at all, these two have conducted 29 trades throughout their storied histories.

While the trades are typically for the likes of cash considerations or draft picks, a few major names in the rivalry’s history have been part of these trades – whether it be Lorne Chabot heading to Montréal for star goalie George Hainsworth in 1933 (so that the Canadiens could field a Francophone netminder), Montréal trading young prospect Ted Kennedy in 1943 before he became a Leafs legend, or Toronto shockingly trading top prospect Russ Courtnall in 1988.

1 – Pick used to select Peter Lee at 12th overall (Round 1, Pick 12)
2 – Pick later traded to Minnesota; used to select Ken Hodge Jr. at 46th overall (Round 3, Pick 4)
3 – Pick used to select Benoît Brunet at 27th overall (Round 2, Pick 6)
4 – Pick later traded back to Toronto; used to select Kent Hulst at 69th overall (Round 4, Pick 6)
5 – Pick used to select Darryl Shannon at 36th overall (Round 2, Pick 15)
6 – Pick used to select Kent Hulst at 69th overall (Round 4, Pick 6)
7 – Pick used to select Mike Doers at 125th overall (Round 6, Pick 20)
8 – Pick used to select Martin Bélanger at 74th overall (Round 3, Pick 22)
9 – Pick used to select Kim Staal at 92nd overall (Round 4, Pick 12)
10 – Pick used to select Mark Flood at 188th overall (Round 6, Pick 21)
11 – Pick later traded to Chicago, Toronto and Boston; used to select Jared Knight at 32nd overall (Round 2, Pick 2)
12 – Pick used to select Jacob Olofsson at 56th overall (Round 2, Pick 25)