Jules Dugal trades
| Montreal Canadiens acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
 | Bill MacKenzie | May 11, 1940 | cash |  |
| Toronto Maple Leafs acquire | Date | Montreal Canadiens acquire | ||
|---|---|---|---|---|
 | $7.5K cash | May 10, 1940 | Murph Chamberlain | |
| Montreal Canadiens acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Bert Gardiner | April 26, 1940 | Claude Bourque |  |
| cash | ||||
| New York Americans acquire | Date | Montreal Canadiens acquire | ||
|---|---|---|---|---|
 | Johnny Gagnon | January 3, 1940 | cash | |
| Boston Bruins acquire | Date | Montreal Canadiens acquire | ||
|---|---|---|---|---|
 | George Brown | November 29, 1939 | cash | |
| Montreal Canadiens acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Earl Robinson | October 11, 1939 | cash | |
| Boston Bruins acquire | Date | Montreal Canadiens acquire | ||
|---|---|---|---|---|
| Herb Cain | October 10, 1939 | Ray Getliffe | |
| Charlie Sands | ||||