This is a list of Boston Bruins-Montreal Canadiens NHL playoff series. To date, Montreal has won 24, Boston 9, of the 33 series. Scores of games won by the series winning team are in bold.
| Season | Round | Result | Game 1 | Game 2 | Game 3 | Game 4 | Game 5 | Game 6 | Game 7 |
|---|---|---|---|---|---|---|---|---|---|
| 1928-29 | Semifinal | Boston 3-0 | 0-1 | 0-1 | 3-2 | — | — | — | — |
| 1929-30 | Final | Montreal 2-0 | 3-0 | 3-4 | — | — | — | — | — |
| 1930-31 | Semifinal | Montreal 3-2 | 4-5 | 1-0 | 3-4 | 3-1 | 2-3 | — | — |
| 1942-43 | Semifinal | Boston 4-1 | 4-5 | 3-5 | 3-2 | 0-4 | 4-5 | — | — |
| 1945-46 | Final | Montreal 4-1 | 3-4 | 2-3 | 4-2 | 2-3 | 3-6 | — | — |
| 1946-47 | Semifinal | Montreal 4-1 | 1-3 | 1-2 | 2-4 | 5-1 | 3-4 | — | — |
| 1951-52 | Semifinal | Montreal 4-3 | 1-5 | 0-4 | 1-4 | 2-3 | 1-0 | 3-2 | 1-3 |
| 1952-53 | Final | Montreal 4-1 | 2-4 | 4-1 | 3-0 | 7-3 | 0-1 | — | — |
| 1953-54 | Semifinal | Montreal 4-0 | 0-2 | 1-8 | 4-3 | 2-0 | — | — | — |
| 1954-55 | Semifinal | Montreal 4-1 | 0-2 | 1-3 | 2-4 | 4-3 | 1-5 | — | — |
| 1956-57 | Final | Montreal 4-1 | 1-5 | 0-1 | 4-2 | 0-2 | 1-5 | — | — |
| 1957-58 | Final | Montreal 4-2 | 1-2 | 5-2 | 3-0 | 1-3 | 2-3 | 5-3 | — |
| 1967-68 | Quarterfinal | Montreal 4-0 | 1-2 | 3-5 | 5-2 | 3-2 | — | — | — |
| 1968-69 | Semifinal | Montreal 4-2 | 2-3 | 3-4 | 0-5 | 2-3 | 2-4 | 2-1 | — |
| 1970-71 | Quarterfinal | Montreal 4-3 | 1-3 | 7-5 | 1-3 | 5-2 | 3-7 | 3-8 | 4-2 |
| 1976-77 | Final | Montreal 4-0 | 3-7 | 0-3 | 4-2 | 2-1 | — | — | — |
| 1977-78 | Final | Montreal 4-2 | 1-4 | 2-3 | 0-4 | 3-4 | 1-4 | 4-1 | — |
| 1978-79 | Semifinal | Montreal 4-3 | 2-4 | 2-5 | 1-2 | 3-4 | 1-5 | 2-5 | 4-5 |
| 1983-84 | Adams Division Semifinal | Montreal 3-0 | 2-1 | 3-1 | 0-5 | — | — | — | — |
| 1984-85 | Adams Division Semifinal | Montreal 3-2 | 5-3 | 3-5 | 4-2 | 6-7 | 0-1 | — | — |
| 1985-86 | Adams Division Semifinal | Montreal 3-0 | 1-3 | 2-3 | 4-3 | — | — | — | — |
| 1986-87 | Adams Division Semifinal | Montreal 4-0 | 2-6 | 3-4 | 5-4 | 4-2 | — | — | — |
| 1987-88 | Adams Division Final | Boston 4-1 | 2-5 | 4-3 | 1-3 | 0-2 | 4-1 | — | — |
| 1988-89 | Adams Division Final | Montreal 4-1 | 2-3 | 2-3 | 5-4 | 2-3 | 2-3 | — | — |
| 1989-90 | Adams Division Final | Boston 4-1 | 0-1 | 4-5 | 6-3 | 1-4 | 1-3 | — | — |
| 1990-91 | Adams Division Final | Boston 4-3 | 1-2 | 4-3 | 3-2 | 2-6 | 1-4 | 2-3 | 1-2 |
| 1991-92 | Adams Division Final | Boston 4-0 | 6-4 | 3-2 | 2-3 | 0-2 | — | — | — |
| 1993-94 | Eastern Quarterfinal | Boston 4-3 | 2-3 | 3-2 | 6-3 | 2-5 | 2-1 | 3-2 | 3-5 |
| 2001-02 | Eastern Quarterfinal | Montreal 4-2 | 5-2 | 4-6 | 3-5 | 5-2 | 2-1 | 1-2 | — |
| 2003-04 | Eastern Quarterfinal | Montreal 4-3 | 0-3 | 1-2 | 2-3 | 4-3 | 5-1 | 2-5 | 2-0 |
| 2007-08 | Eastern Quarterfinal | Montreal 4-3 | 1-4 | 2-3 | 1-2 | 1-0 | 5-1 | 4-5 | 0-5 |
| 2008-09 | Eastern Quarterfinal | Boston 4-0 | 2-4 | 1-5 | 4-2 | 4-1 | |||
| 2010-11 | Eastern Quarterfinal | Boston 4-3 | 0-2 | 1-3 | 4-2 | 5-4 | 1-2 | 2-1 | 4-3 |
| 2013-14 | Eastern Semifinal | Montreal 4-3 | 4-3 | 3-5 | 4-2 | 0-1 | 2-4 | 4-0 | 3-1 |