Notable deals
| Montreal Canadiens acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
 | Lou Fontinato | June 13, 1969 | Doug Harvey |  |
| St. Louis Blues acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
 | Phil Goyette | June 10, 1969 | 1969 1st round pick (#8-Andre Dupont) | |
| Montreal Canadiens acquire | Date | Detroit Red Wings acquire | ||
|---|---|---|---|---|
| Bart Crashley | June 6, 1969 | Garry Monahan |  |
| Pete Mahovlich | Doug Piper | |||
| Boston Bruins acquire | Date | Los Angeles Kings acquire | ||
|---|---|---|---|---|
 | Ken Turlik | May 14, 1969 | Ross Lonsberry |  |
| 1971 1st round pick (#6-Ron Jones) | Eddie Shack | |||
| 1973 1st round pick (#6-Andre Savard) | ||||
| Los Angeles Kings acquire | Date | Detroit Red Wings acquire | ||
|---|---|---|---|---|
| Jimmy Peters Jr. | October 10, 1968 | Terry Sawchuk | |
| Montreal Canadiens acquire | Date | Minnesota North Stars acquire | ||
|---|---|---|---|---|
| 1972 1st round pick (#8-Dave Gardner) | June 10, 1968 | Danny Grant |  |
| cash | Claude D. Larose | |||
| future considerations (Marshall Johnston) | future considerations (Bob Murdoch) | |||
| Toronto Maple Leafs acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
 | Pierre Pilote | May 23, 1968 | Jim Pappin |  |
| Boston Bruins acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| cash | May 21, 1968 | Jean Pronovost |  |
| John Arbour | ||||
| Toronto Maple Leafs acquire | Date | Detroit Red Wings acquire | ||
|---|---|---|---|---|
| Norm Ullman | March 3, 1968 | Garry Unger | |
| Floyd Smith | Pete Stemkowski | |||
| Paul Henderson | Frank Mahovlich | |||
| Doug Barrie | rights to Carl Brewer | |||
| Toronto Maple Leafs acquire | Date | Minnesota North Stars acquire | ||
|---|---|---|---|---|
| Murray Hall | December 23, 1967 | Milan Marcetta | |
| Duke Harris | Jean-Paul Parise | |||
| Don Johns | ||||
| Len Lunde | ||||
| Ted Taylor | ||||
| loan of Carl Wetzel | ||||
| St. Louis Blues acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Barclay Plager | November 27, 1967 | Ron Attwell | |
| Red Berenson | Ron Stewart | |||
| Toronto Maple Leafs acquire | Date | California Golden Seals (Oakland) acquire | ||
|---|---|---|---|---|
| Jean-Paul Parise | October 12, 1967 | Gerry Ehman | .gif){kind=small} |
| Bryan Hextall Jr. | ||||
| Montreal Canadiens acquire | Date | Minnesota North Stars acquire | ||
|---|---|---|---|---|
| cash | June 7, 1967 | Bill Masterton | |
| St. Louis Blues acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Tim Ecclestone | June 6, 1967 | Rod Seiling | |
| Gord Kannegiesser | ||||
| Bob Plager | ||||
| Gary Sabourin | ||||
| Boston Bruins acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Ken Hodge Sr. | May 15, 1967 | Jack Norris | |
| Phil Esposito | Pit Martin | |||
| Fred Stanfield | Gilles Marotte | |||
| Toronto Maple Leafs acquire | Date | Boston Bruins acquire | ||
|---|---|---|---|---|
| Murray Oliver | May 15, 1967 | Eddie Shack | |
| cash | ||||
| Toronto Maple Leafs acquire | Date | Boston Bruins acquire | ||
|---|---|---|---|---|
| Andy Hebenton | June 8, 1965 | Ron Stewart | |
| Orland Kurtenbach | ||||
| Pat Stapleton | ||||
| Detroit Red Wings acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Ted Lindsay | October 14, 1964 | cash | |
| Toronto Maple Leafs acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Don McKenney | February 22, 1964 | Bob Nevin | |
| Andy Bathgate | Dick Duff | |||
| Bill Collins | ||||
| Arnie Brown | ||||
| Rod Seiling | ||||
| Toronto Maple Leafs acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Eddie Shack | November 7, 1960 | Pat Hannigan | |
| Johnny Wilson | ||||