| Oct 2, 1968 Wed | Preseason | NY Rangers | Boston | Hextall-Gibbs Hextall-Awrey |
| Oct 6, 1968 Sun | Preseason | Montreal | Boston | Add Fight |
| Oct 11, 1968 Fri | | Detroit | Boston | Mahovlich-Smith Baun-Doak |
| Oct 13, 1968 Sun | | Philadelphia | Boston | Heiskala-Sanderson Brawl at 19:51 Heiskala-Hodge |
| Oct 16, 1968 Wed | | Boston | Oakland | Add Fight |
| Oct 17, 1968 Thu | | Boston | Los Angeles | Add Fight |
| Oct 19, 1968 Sat | | Boston | Pittsburgh | Add Fight |
| Oct 24, 1968 Thu | | St. Louis | Boston | Add Fight |
| Oct 26, 1968 Sat | | Boston | Toronto | (Cheap) Williams-unknown Sanderson-Horton (3) Shack-Dorey (3) |
| Oct 27, 1968 Sun | | Montreal | Boston | Add Fight |
| Oct 30, 1968 Wed | | Boston | Minnesota | Add Fight |
| Oct 31, 1968 Thu | | Boston | Detroit | Add Fight |
| Nov 3, 1968 Sun | | Chicago | Boston | Mikita-Doak |
| Nov 6, 1968 Wed | | Philadelphia | Boston | Add Fight |
| Nov 10, 1968 Sun | | St. Louis | Boston | Brawl at 28:56 Cameron-Orr Plager-Green (Cheap) Cameron-Cheevers Brawl at 35:03 Cameron-Smith |
| Nov 13, 1968 Wed | | Boston | Toronto | Add Fight |
| Nov 14, 1968 Thu | | Boston | Philadelphia | Hodge-Nolet Orr-Dornhoefer Orr-Dornhoefer |
| Nov 17, 1968 Sun | | Oakland | Boston | Vadnais-Sanderson |
| Nov 21, 1968 Thu | | Los Angeles | Boston | Add Fight |
| Nov 23, 1968 Sat | | NY Rangers | Boston | Add Fight |
| Nov 24, 1968 Sun | | Toronto | Boston | Dorey-Shack |
| Nov 27, 1968 Wed | | Boston | St. Louis | McKenzie-Plager |
| Nov 30, 1968 Sat | | NY Rangers | Boston | Add Fight |
| Dec 1, 1968 Sun | | Minnesota | Boston | Connelly-Awrey |
| Dec 5, 1968 Thu | | Montreal | Boston | Event at 0:00 |
| Dec 7, 1968 Sat | | Detroit | Boston | Mahovlich-Orr |
| Dec 8, 1968 Sun | | Boston | Chicago | Add Fight |
| Dec 11, 1968 Wed | | Boston | NY Rangers | Scrum at 44:28 |
| Dec 14, 1968 Sat | | Chicago | Boston | Marotte-Awrey Schmautz-Shack Young-Sather |
| Dec 15, 1968 Sun | | Pittsburgh | Boston | Add Fight |
| Dec 19, 1968 Thu | | Los Angeles | Boston | Add Fight |
| Dec 21, 1968 Sat | | Boston | Montreal | McKenzie-Richard |
| Dec 22, 1968 Sun | | Montreal | Boston | (Cheap) unknown-Esposito |
| Dec 25, 1968 Wed | | Oakland | Boston | Vadnais-Hodge |
| Dec 28, 1968 Sat | | Boston | St. Louis | Add Fight |
| Dec 29, 1968 Sun | | Boston | Detroit | Add Fight |
| Jan 2, 1969 Thu | | Boston | NY Rangers | Sather-Balon Green-Brown |
| Jan 4, 1969 Sat | | Boston | Minnesota | Add Fight |
| Jan 9, 1969 Thu | | Toronto | Boston | Walton-Sather Brawl at 8:50 Pilote-McKenzie Dorey-Smith Dorey-Cheevers Gamble-Orr |
| Jan 11, 1969 Sat | | Boston | Montreal | Add Fight |
| Jan 12, 1969 Sun | | Pittsburgh | Boston | Add Fight |
| Jan 15, 1969 Wed | | Boston | Toronto | (Cheap) Orr-Quinn Harrison-Quinn |
| Jan 16, 1969 Thu | | Minnesota | Boston | Add Fight |
| Jan 18, 1969 Sat | | Boston | Philadelphia | Add Fight |
| Jan 19, 1969 Sun | | Toronto | Boston | Injury Event Walton-McKenzie |
| Jan 23, 1969 Thu | | Boston | Detroit | Cashman-LeClerc |
| Jan 25, 1969 Sat | | St. Louis | Boston | Add Fight |
| Jan 26, 1969 Sun | | Minnesota | Boston | Larose-Sather |
| Jan 29, 1969 Wed | | Boston | Oakland | (Rough) Sanderson-Lacombe |
| Jan 30, 1969 Thu | | Boston | Los Angeles | (Rough) Hodge-Hughes Hodge-Hughes |
| Feb 2, 1969 Sun | | Detroit | Boston | Add Fight |
| Feb 5, 1969 Wed | | Boston | Chicago | Add Fight |
| Feb 6, 1969 Thu | | Boston | St. Louis | Sather-Plager |
| Feb 8, 1969 Sat | | Philadelphia | Boston | Mini-Brawl at 34:44 Abuse at 44:34 (Rough) Hale-Esposito |
| Feb 9, 1969 Sun | | Oakland | Boston | Add Fight |
| Feb 11, 1969 Tue | | Chicago | Boston | Add Fight |
| Feb 15, 1969 Sat | | Boston | Montreal | Add Fight |
| Feb 16, 1969 Sun | | Boston | Chicago | Webster-Hull Awrey-Mikita |
| Feb 19, 1969 Wed | | Boston | Pittsburgh | Add Fight |
| Feb 23, 1969 Sun | | Boston | NY Rangers | Awrey-Hextall Awrey-Fleming Brawl at 35:28 |
| Feb 26, 1969 Wed | | Boston | Los Angeles | Add Fight |
| Feb 27, 1969 Thu | | Boston | Oakland | Add Fight |
| Mar 1, 1969 Sat | | NY Rangers | Boston | Scrum at 5:32 (Rough) unknown-McKenzie |
| Mar 2, 1969 Sun | | Pittsburgh | Boston | Speer-Sanderson |
| Mar 5, 1969 Wed | | Detroit | Boston | Add Fight |
| Mar 8, 1969 Sat | | Boston | Detroit | Add Fight |
| Mar 9, 1969 Sun | | Los Angeles | Boston | (Cheap) unknown-Hodge |
| Mar 11, 1969 Tue | | Boston | Minnesota | Add Fight |
| Mar 13, 1969 Thu | | Boston | Philadelphia | (Rough) McKenzie-Gendron |
| Mar 15, 1969 Sat | | Boston | Toronto | Cashman-Ley (6) Orr-Quinn |
| Mar 16, 1969 Sun | | Toronto | Boston | Selby-McKenzie Kennedy-Green |
| Mar 19, 1969 Wed | | Boston | Pittsburgh | Cashman-Pratt Esposito-McCreary |
| Mar 20, 1969 Thu | | Chicago | Boston | Marotte-Awrey Brawl at 56:45 |
| Mar 22, 1969 Sat | | Boston | Chicago | Add Fight |
| Mar 23, 1969 Sun | | Boston | NY Rangers | Add Fight |
| Mar 27, 1969 Thu | | NY Rangers | Boston | Add Fight |
| Mar 29, 1969 Sat | | Boston | Montreal | Add Fight |
| Mar 30, 1969 Sun | | Montreal | Boston | Harris-Orr |
| Apr 2, 1969 Wed | QF | Game 1 | Toronto | Boston | (Rough) Kennedy-McKenzie Horton-Sanderson (Cheap) Quinn-Orr (10) Crowd Trouble at 38:03 Dorey-Shack Brawl at 46:14 Kennedy-Cheevers Kennedy-Bucyk Abuse at 46:14 (8) Kennedy-Cheevers (8) Crowd Trouble at 46:14 (10) Kennedy-McKenzie (7.5) |
| Apr 3, 1969 Thu | QF | Game 2 | Toronto | Boston | Brawl at 29:08 Mickey-Awrey Quinn-Green |
| Apr 5, 1969 Sat | QF | Game 3 | Boston | Toronto | Westfall-Ley Esposito-Pelyk (Rough) Shack-Ellis |
| Apr 6, 1969 Sun | QF | Game 4 | Boston | Toronto | Add Fight |
| Apr 10, 1969 Thu | SF | Game 1 | Boston | Montreal | Brawl at 6:47 Sather-Cournoyer (6.3) Sanderson-Duff (2) |
| Apr 13, 1969 Sun | SF | Game 2 | Boston | Montreal | Add Fight |
| Apr 17, 1969 Thu | SF | Game 3 | Montreal | Boston | Add Fight |
| Apr 20, 1969 Sun | SF | Game 4 | Montreal | Boston | Harris-Sather |
| Apr 22, 1969 Tue | SF | Game 5 | Boston | Montreal | Add Fight |
| Apr 24, 1969 Thu | SF | Game 6 | Montreal | Boston | Ferguson-Awrey (3) |