Larry Jeffrey trades
| Detroit Red Wings acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
 | Larry Jeffrey | June 17, 1969 | Terry Sawchuk |  |
| Sandy Snow | ||||
| Pittsburgh Penguins acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
 | Paul Andrea | June 6, 1967 | Larry Jeffrey | |
| Frank Francis | ||||
| George Konik | ||||
| Dunc McCallum | ||||
| Toronto Maple Leafs acquire | Date | Detroit Red Wings acquire | ||
|---|---|---|---|---|
 | Autry Erickson | May 20, 1965 | Andy Bathgate | |
| Larry Jeffrey | Billy Harris | |||
| Eddie Joyal | Gary Jarrett | |||
| Lowell MacDonald | ||||
| Marcel Pronovost | ||||