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.
| to Montréal | Date | to Toronto |
|---|---|---|
| Harry Cameron | Jan. 14, 1920 | Goldie Prodgers |
| Goldie Prodgers Joe Matte |
Nov. 27, 1920 | Harry Cameron |
| George Patterson | Feb. 8, 1928 | cash |
| Lorne Chabot | Oct. 1, 1933 | George Hainsworth |
| Murph Chamberlain | May 10, 1940 | $7,500 |
| Joe Benoit | Jun. 7, 1940 | Frank Eddolls |
| Gordie Drillon | Oct. 4, 1942 | $30,000 |
| Frank Eddolls | Sep. 10, 1943 | Ted Kennedy |
| cash | Nov. 24, 1944 | John Mahaffy |
| Gerry Brown John Mahaffy |
Sep. 21, 1946 | Dutch Hiller Vic Lynn |
| John McCormack | Sep. 23, 1951 | cash |
| cash | Sep. 30, 1957 | Paul Masnick |
| Gary Collins | Nov. 1, 1959 | $10,000 |
| Al MacNeil cash |
Jun. 7, 1960 | Stan Smrke Guy Rousseau |
| Guy Rousseau | Jun. 1, 1961 | Norm Corcoran |
| Terry Clancy | Dec. 23, 1970 | cash |
| cash | Aug. 30, 1971 | Terry Clancy |
| 1976 1st Rd. Pick1 |
Jun. 17, 1975 | Wayne Thomas |
| Doug Jarvis | Jun. 26, 1975 | Greg Hubick |
| Robert Picard | Mar. 10, 1981 | Michel Larocque |
| 1984 3rd Rd. Pick2 1986 2nd Rd. Pick3 |
Dec. 17, 1982 | Dan Daoust Gaston Gingras |
| 1986 4th Rd. Pick4 |
Aug. 17, 1984 | Bill Root |
| Gaston Gingras | Feb. 14, 1985 | Larry Landon |
| Dom Campedelli | Sep. 18, 1985 | 1986 2nd Rd. Pick5 1986 4th Rd. Pick6 |
| Russ Courtnall | Nov. 7, 1988 | John Kordic 1989 6th Rd. Pick7 |
| 1994 3rd Rd. Pick8 |
Aug. 20, 1992 | Sylvain Lefebvre |
| 1996 4th Rd. Pick9 |
Apr. 6, 1995 | Paul DiPietro |
| 2003 6th Rd. Pick10 |
Mar. 11, 2003 | Doug Gilmour |
| Greg Pateryn 2010 2nd Rd. Pick11 |
Jul. 3, 2008 | Mikhail Grabovski |
| Kerby Rychel Rinat Valiev 2018 2nd Rd. Pick12 |
Feb. 25, 2018 | Kyle Baun Tomas Plekanec |
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 on September 18, 1985
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, then 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)
Two Solitudes 