| Year | Opponent | W/L | Series Result | Round |
| 1927 | Chicago | W | 10-5 (TG) | Quarterfinals |
| NY Rangers | W | 3-1 (TG) | Semifinals |
| Ottawa | L | 2-0 | Stanley Cup Final |
| 1928 | NY Rangers | L | 5-2 (TG) | Semifinals |
| 1929 | Monteal | W | 3-0 | Semifinals |
| NY Rangers | W | 2-0 | STANLEY CUP CHAMPIONS |
| 1930 | Montreal Maroons | W | 3-1 | Semifinals |
| Montreal | L | 2-0 | Stanley Cup Final |
| 1931 | Montreal | L | 3-2 | Semifinals |
| 1933 | Toronto | L | 3-2 | Semifinals |
| 1935 | Toronto | L | 3-1 | Semifinals |
| 1936 | Toronto | L | 8-6 (TG) | Quarterfinals |
| 1937 | Montreal Maroons | L | 2-1 | Quarterfinals |
| 1938 | Toronto | L | 3-0 | Semifinals |
| 1939 | NY Rangers | W | 4-3 | Semifinals |
| Toronto | W | 4-1 | STANLEY CUP CHAMPIONS |
| 1940 | NY Rangers | L | 4-2 | Semifinals |
| 1941 | Toronto | W | 4-3 | Semifinal |
| Detroit | W | 4-0 | STANLEY CUP CHAMPIONS |
| 1942 | Chicago | W | 2-1 | Quarterfinals |
| Detroit | L | 2-0 | Semifinals |
| 1943 | Montreal | W | 4-1 | Semifinals |
| Detroit | L | 4-0 | Stanley Cup Final |
| 1945 | Detroit | L | 4-3 | Semifinals |
| 1946 | Detroit | W | 4-1 | Semifinals |
| Montreal | L | 4-1 | Stanley Cup Final |
| 1947 | Montreal | L | 4-1 | Semifinals |
| 1948 | Toronto | L | 4-1 | Semifinals |
| 1949 | Toronto | L | 4-1 | Semifinals |
| 1951 | Toronto | L | 4-1 | Semifinals |
| 1952 | Montreal | L | 4-3 | Semifinals |
| 1953 | Detroit | W | 4-2 | Semifinals |
| Montreal | L | 4-1 | Stanley Cup Final |
| 1954 | Montreal | L | 4-0 | Semifinals |
| 1955 | Montreal | L | 4-1 | Semifinals |
| 1957 | Detroit | W | 4-1 | Semifinals |
| Montreal | L | 4-1 | Stanley Cup Final |
| 1958 | NY Rangers | W | 4-2 | Semifinals |
| Montreal | L | 4-2 | Stanley Cup Final |
| 1959 | Toronto | L | 4-3 | Semifinals |
| 1968 | Montreal | L | 4-0 | Quarterfinals |
| 1969 | Toronto | W | 4-0 | Quarterfinals |
| Montreal | L | 4-2 | Semifinals |
| 1970 | NY Rangers | W | 4-2 | Quarterfinals |
| Chicago | W | 4-0 | Semifinals |
| St. Louis | W | 4-0 | STANLEY CUP CHAMPIONS |
| 1971 | Montreal | L | 4-3 | Quarterfinals |
| 1972 | Toronto | W | 4-1 | Quarterfinals |
| St. Louis | W | 4-0 | Semifinals |
| NY Rangers | W | 4-2 | STANLEY CUP CHAMPIONS |
| 1973 | NY Rangers | L | 4-1 | Quarterfinals |
| 1974 | Toronto | W | 4-0 | Quarterfinals |
| Chicago | W | 4-2 | Semifinals |
| Philadelphia | L | 4-2 | Stanley Cup Final |
| 1975 | Chicago | L | 2-1 | Preliminary Round |
| 1976 | Los Angeles | W | 4-3 | Quarterfinals |
| Philadelphia | L | 4-1 | Semifinals |
| 1977 | Los Angeles | W | 4-2 | Quarterfinals |
| Philadelphia | W | 4-0 | Semifinals |
| Montreal | L | 4-0 | Stanley Cup Final |
| 1978 | Chicago | W | 4-0 | Quarterfinals |
| Philadelphia | W | 4-1 | Semifinals |
| Montreal | L | 4-2 | Stanley Cup Final |
| 1979 | Pittsburgh | W | 4-0 | Quarterfinals |
| Montreal | L | 4-3 | Semifinals |
| 1980 | Pittsburgh | W | 3-2 | Preliminary Round |
| NY Islanders | L | 4-1 | Quarterfinals |
| 1981 | Minnesota Nstars | L | 3-0 | Preliminary Round |
| 1982 | Buffalo | W | 3-1 | Adams Division Semifinals |
| Quebec | L | 4-3 | Adams Division Final |
| 1983 | Quebec | W | 3-1 | Adams Division Semifinals |
| Buffalo | W | 4-3 | Adams Division Final |
| NY Islanders | L | 4-2 | Wales Conference Final |
| 1984 | Montreal | L | 3-0 | Adams Division Semifinals |
| 1985 | Montreal | L | 3-2 | Adams Division Semifinals |
| 1986 | Montreal | L | 3-0 | Adams Division Semifinals |
| 1987 | Montreal | L | 4-0 | Adams Division Semifinals |
| 1988 | Buffalo | W | 4-2 | Adams Division Semifinals |
| Montreal | W | 4-1 | Adams Division Final |
| New Jersey | W | 4-3 | Wales Conference Final |
| Edmonton | L | 4-0* | Stanley Cup Final |
| 1989 | Buffalo | W | 4-1 | Adams Division Semifinals |
| Montreal | L | 4-1 | Adams Division Final |
| 1990 | Hartford | W | 4-3 | Adams Division Semifinals |
| Montreal | W | 4-1 | Adams Division Final |
| Washington | W | 4-0 | Wales Conference Final |
| Edmonton | L | 4-1 | Stanley Cup Final |
| 1991 | Hartford | W | 4-2 | Adams Division Semifinals |
| Montreal | W | 4-3 | Adams Division Final |
| Pittsburgh | L | 4-2 | Wales Conference Final |
| 1992 | Buffalo | W | 4-3 | Adams Division Semifinals |
| Montreal | W | 4-0 | Adams Division Final |
| Pittsburgh | L | 4-0 | Wales Conference Final |
| 1993 | Buffalo | L | 4-0 | Adams Division Semifinals |
| 1994 | Montreal | W | 4-3 | Eastern Conference Quarterfinal |
| New Jersey | L | 4-2 | Eastern Conference Semifinals |
| 1995 | New Jersey | L | 4-1 | Eastern Conference Quarterfinal |
| 1996 | Florida | L | 4-1 | Eastern Conference Quarterfinal |
| 1998 | Washington | L | 4-2 | Eastern Conference Quarterfinal |
| 1999 | Carolina | W | 4-2 | Eastern Conference Quarterfinal |
| Buffalo | L | 4-2 | Eastern Conference Semifinals |
| 2002 | Montreal | L | 4-2 | Eastern Conference Quarterfinal |
| 2003 | New Jersey | L | 4-1 | Eastern Conference Quarterfinal |
| 2004 | Montreal | L | 4-3 | Eastern Conference Quarterfinal |
| 2008 | Montreal | L | 4-3 | Eastern Conference Quarterfinal |
| 2009 | Montreal | W | 4-0 | Eastern Conference Quarterfinal |
| Carolina | L | 4-3 | Eastern Conference Semifinals |
| 2010 | Buffalo | W | 4-2 | Eastern Conference Quarterfinal |
| Philadelphia | L | 4-3 | Eastern Conference Semifinals |
| 2011 | Montreal | W | 4-3 | Eastern Conference Quarterfinal |
| Philadelphia | W | 4-0 | Eastern Conference Semifinals |
| Tampa Bay | W | 4-3 | Eastern Conference Final |
| Vancouver | W | 4-3 | STANLEY CUP CHAMPIONS |
| 2012 | Washington | L | 4-3 | Eastern Conference Quarterfinal |
| 2013 | Toronto | W | 4-3 | Eastern Conference Quarterfinal |
