| Year | Opponent | W/L | Series Result | Round |
| 1918 | Toronto Arenas | L | 10-7 (TG) N | HL Final |
| 1919 | Ottawa | W | 4-1 N | HL Final |
| Seattle (Stanl | ey Cu | p Final cancelled du | e to flu epidemic) |
| 1923 | Ottawa | L | 3-2 (TG) N | HL Final |
| 1924 | Ottawa | W | 5-2 (TG) N | HL Final |
| Vancouver Mill. | W | 2-0 S | tanley Cup Series 1 |
| Calgary | W | 2-0 S | TANLEY CUP CHAMPIONS |
| 1925 | Toronto St. Pats | W | 5-2 (TG) N | HL Semifinals |
| Victoria | L | 3-1 S | tanley Cup Final |
| 1927 | Montreal Maroons | W | 2-1 (TG) Q | uarterfinals |
| Ottawa | L | 5-1 (TG) S | emifinals |
| 1928 | Montreal Maroons | L | 3-2 (TG) S | emifinals |
| 1929 | Boston | L | 3-0 S | emifinals |
| 1930 | Chicago | W | 3-2 (TG) Q | uarterfinals |
| NY Rangers | W | 2-0 S | emifinals |
| Boston | W | 2-0 S | TANLEY CUP CHAMPIONS |
| 1931 | Boston | W | 3-2 S | emifinals |
| Chicago | W | 3-2 S | TANLEY CUP CHAMPIONS |
| 1932 | NY Rangers | L | 3-1 S | emifinals |
| 1933 | NY Rangers | L | 8-5 (TG) Q | uarterfinals |
| 1934 | Chicago | L | 4-3 (TG) Q | uarterfinals |
| 1935 | NY Rangers | L | 6-5 (TG) Q | uarterfinals |
| 1937 | Detroit | L | 3-2 S | emifinals |
| 1938 | Chicago | L | 2-1 Q | uarterfinals |
| 1939 | Detroit | L | 2-1 Q | uarterfinals |
| 1941 | Chicago | L | 2-1 Q | uarterfinals |
| 1942 | Detroit | L | 2-1 Q | uarterfinals |
| 1943 | Boston | L | 4-1 S | emifinals |
| 1944 | Toronto | W | 4-1 S | emifinals |
| Chicago | W | 4-0 S | TANLEY CUP CHAMPIONS |
| 1945 | Toronto | L | 4-2 S | emifinals |
| 1946 | Chicago | W | 4-0 S | emifinals |
| Boston | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1947 | Boston | W | 4-1 S | emifinals |
| Toronto | L | 4-2 S | tanley Cup Final |
| 1949 | Detroit | L | 4-3 S | emifinals |
| 1950 | NY Rangers | L | 4-1 S | emifinals |
| 1951 | Detroit | W | 4-2 S | emifinals |
| Toronto | L | 4-1 S | tanley Cup Final |
| 1952 | Boston | W | 4-3 S | emifinals |
| Detroit | L | 4-0 S | tanley Cup Final |
| 1953 | Chicago | W | 4-3 S | emifinals |
| Boston | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1954 | Boston | W | 4-0 S | emifinals |
| Detroit | L | 4-3 S | tanley Cup Final |
| 1955 | Boston | W | 4-1 S | emifinals |
| Detroit | L | 4-3 S | tanley Cup Final |
| 1956 | NY Rangers | W | 4-1 S | emifinals |
| Detroit | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1957 | NY Rangers | W | 4-1 S | emifinals |
| Boston | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1958 | Detroit | W | 4-0 S | emifinals |
| Boston | W | 4-2 S | TANLEY CUP CHAMPIONS |
| 1959 | Chicago | W | 4-2 S | emifinals |
| Toronto | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1960 | Chicago | W | 4-0 S | emifinals |
| Toronto | W | 4-0 S | TANLEY CUP CHAMPIONS |
| 1961 | Chicago | L | 4-2 S | emifinals |
| 1962 | Chicago | L | 4-2 S | emifinals |
| 1963 | Toronto | L | 4-1 S | emifinals |
| 1964 | Montreal | L | 4-3 S | emifinals |
| 1965 | Montreal | W | 4-2 S | emifinals |
| Chicago | W | 4-3 S | TANLEY CUP CHAMPIONS |
| 1966 | Toronto | W | 4-0 S | emifinals |
| Detroit | W | 4-2 S | TANLEY CUP CHAMPIONS |
| 1967 | NY Rangers | W | 4-0 S | emifinals |
| Toronto | L | 4-2 S | tanley Cup Final |
| 1968 | Boston | W | 4-0 Q | uarterfinals |
| Chicago | W | 4-1 S | emifinals |
| St. Louis | W | 4-0 S | TANLEY CUP CHAMPIONS |
| 1969 | NY Rangers | W | 4-0 Q | uarterfinals |
| Boston | W | 4-2 S | emifinals |
| St. Louis | W | 4-0 S | TANLEY CUP CHAMPIONS |
| 1971 | Boston | W | 4-3 Q | uarterfinals |
| Minnesota NStars | W | 4-2 S | emifinals |
| Chicago | W | 4-3 S | TANLEY CUP CHAMPIONS |
| 1972 | NY Rangers | L | 4-1 Q | uarterfinals |
| 1973 | Buffalo | W | 4-2 Q | uarterfinals |
| Philadelphia | W | 4-1 S | emifinals |
| Chicago | W | 4-2 S | TANLEY CUP CHAMPIONS |
| 1974 | NY Rangers | L | 4-2 Q | uarterfinals |
| 1975 | Vancouver | W | 4-1 Q | uarterfinals |
| Buffalo | L | 4-2 S | emifinals |
| 1976 | Chicago | W | 4-0 Q | uarterfinals |
| NY Islanders | W | 4-1 S | emifinals |
| Philadelphia | W | 4-0 S | TANLEY CUP CHAMPIONS |
| 1977 | St. Louis | W | 4-0 Q | uarterfinals |
| NY Islanders | W | 4-2 S | emifinals |
| Boston | W | 4-0 S | TANLEY CUP CHAMPIONS |
| 1978 | Detroit | W | 4-1 Q | uarterfinals |
| Toronto | W | 4-0 S | emifinals |
| Boston | W | 4-2 S | TANLEY CUP CHAMPIONS |
| 1979 | Toronto | W | 4-0 Q | uarterfinals |
| Boston | W | 4-3 S | emifinals |
| NY Rangers | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1980 | Hartford | W | 3-0 P | reliminary Round |
| Minnesota NStars | L | 4-3 Q | uarterfinals |
| 1981 | Edmonton | L | 3-0 P | reliminary Round |
| 1982 | Quebec | L | 3-2 A | dams Division Semifinals |
| 1983 | Buffalo | L | 3-0 A | dams Division Semifinals |
| 1984 | Boston | W | 3-0 A | dams Division Semifinals |
| Quebec | W | 4-2 A | dams Division Final |
| NY Islanders | L | 4-2 W | ales Conference Final |
| 1985 | Boston | W | 3-2 A | dams Division Semifinals |
| Quebec | L | 4-3 A | dams Division Final |
| 1986 | Boston | W | 3-0 A | dams Division Semifinals |
| Hartford | W | 4-3 A | dams Division Final |
| NY Rangers | W | 4-1 W | ales Conference Final |
| Calgary | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1987 | Boston | W | 4-0 A | dams Division Semifinals |
| Quebec | W | 4-3 A | dams Division Final |
| Philadelphia | L | 4-2 W | ales Conference Final |
| 1988 | Hartford | W | 4-2 A | dams Division Semifinals |
| Boston | L | 4-1 A | dams Division Final |
| 1989 | Hartford | W | 4-0 A | dams Division Semifinals |
| Boston | W | 4-1 A | dams Division Final |
| Philadelphia | W | 4-2 W | ales Conference Final |
| Calgary | L | 4-2 S | tanley Cup Final |
| 1990 | Buffalo | W | 4-2 A | dams Division Semifinals |
| Boston | L | 4-1 A | dams Division Final |
| 1991 | Buffalo | W | 4-2 A | dams Division Semifinals |
| Boston | L | 4-3 A | dams Divison Final |
| 1992 | Hartford | W | 4-3 A | dams Division Semifinals |
| Boston | L | 4-0 A | dams Division Final |
| 1993 | Quebec | W | 4-2 A | dams Division Semifinals |
| Buffalo | W | 4-0 N | orris Division Final |
| NY Islanders | W | 4-1 W | ales Conference Final |
| Los Angeles | W | 4-1 S | TANLEY CUP CHAMPIONS |
| 1994 | Boston | L | 4-3 E | astern Conference Quarterfinals |
| 1996 | NY Rangers | L | 4-2 E | astern Conference Quarterfinals |
| 1997 | New Jersey | L | 4-1 E | astern Conference Quarterfinals |
| 1998 | Pittsburgh | W | 4-2 E | astern Conference Quarterfinals |
| Buffalo | L | 4-0 E | astern Conference Semifinals |
| 2002 | Boston | W | 4-2 E | astern Conference Quarterfinals |
| Carolina | L | 4-2 E | astern Conference Semifinals |
| 2004 | Boston | W | 4-3 E | astern Conference Quarterfinals |
| Tampa Bay | L | 4-0 E | astern Conference Semifinals |
| 2006 | Carolina | L | 4-2 E | astern Conference Quarterfinals |
| 2008 | Boston | W | 4-3 E | astern Conference Quarterfinals |
| Philadelphia | L | 4-1 E | astern Conference Semifinals |
| 2009 | Boston | L | 4-0 E | astern Conference Quarterfinals |
| 2010 | Washington | W | 4-3 E | astern Conference Quarterfinals |
| Pittsburgh | W | 4-3 E | astern Conference Semifinals |
| Philadelphia | L | 4-1 E | astern Conference Final |
| 2011 | Boston | L | 4-3 E | astern Conference Quarterfinals |
| 2013 | Ottawa | L | 4-1 E | astern Conference Quarterfinals |
