| Year | Opponent | W/L | Series Result | Round |
| 1929 | Toronto | L | 2-1 (TG) | Quarterfinals |
| 1932 | Montreal Maroons | L | 3-1 (TG) | Quarterfinals |
| 1933 | Montreal Maroons | W | 5-2 (TG) | Quarterfinals |
| NY Rangers | L | 6-3 (TG) | Semifinals |
| 1934 | Toronto | W | 3-2 | Semifinals |
| Chicago | L | 3-1 | Stanley Cup Final |
| 1936 | Montreal Maroons | W | 3-0 | Semifinals |
| Toronto | W | 3-1 | STANLEY CUP CHAMPIONS |
| 1937 | Montreal | W | 3-2 | Semifinals |
| NY Rangers | W | 3-2 | STANLEY CUP CHAMPIONS |
| 1939 | Montreal | W | 2-1 | Quarterfinals |
| Toronto | L | 2-1 | Semifinals |
| 1940 | NY Americans | W | 2-1 | Quarterfinals |
| Toronto | L | 2-0 | Semifinals |
| 1941 | NY Rangers | W | 2-1 | Quarterfinals |
| Chicago | W | 2-0 | Semifinals |
| Boston | L | 4-0 | Stanley Cup Final |
| 1942 | Montreal | W | 2-1 | Quarterfinals |
| Boston | W | 2-0 | Semifinals |
| Toronto | L | 4-3 | Stanley Cup Final |
| 1943 | Toronto | W | 4-2 | Semifinals |
| Boston | W | 4-0 | STANLEY CUP CHAMPIONS |
| 1944 | Chicago | L | 4-1 | Semifinals |
| 1945 | Boston | W | 4-3 | Semifinals |
| Toronto | L | 4-3 | Stanley Cup Final |
| 1946 | Boston | L | 4-1 | Semifinals |
| 1947 | Toronto | L | 4-1 | Semifinals |
| 1948 | NY Rangers | W | 4-2 | Semifinals |
| Toronto | L | 4-0 | Stanley Cup Final |
| 1949 | Montreal | W | 4-3 | Semifinals |
| Toronto | L | 4-0 | Stanley Cup Final |
| 1950 | Toronto | W | 4-3 | Semifinals |
| NY Rangers | W | 4-3 | STANLEY CUP CHAMPIONS |
| 1951 | Montreal | L | 4-2 | Semifinals |
| 1952 | Toronto | W | 4-0 | Semifinals |
| Montreal | W | 4-0 | STANLEY CUP CHAMPIONS |
| 1953 | Boston | L | 4-2 | Semifinals |
| 1954 | Toronto | W | 4-1 | Semifinals |
| Montreal | W | 4-3 | STANLEY CUP CHAMPIONS |
| 1955 | Toronto | W | 4-0 | Semifinals |
| Montreal | W | 4-3 | STANLEY CUP CHAMPIONS |
| 1956 | Toronto | W | 4-1 | Semifinals |
| Montreal | L | 4-1 | Stanley Cup Final |
| 1957 | Boston | L | 4-1 | Semifinals |
| 1958 | Montreal | L | 4-0 | Semifinals |
| 1960 | Toronto | L | 4-2 | Semifinals |
| 1961 | Toronto | W | 4-1 | Semifinals |
| Chicago | L | 4-2 | Stanley Cup Final |
| 1963 | Chicago | W | 4-2 | Semifinals |
| Toronto | L | 4-1 | Stanley Cup Final |
| 1964 | Chicago | W | 4-3 | Semifinals |
| Toronto | L | 4-3 | Stanley Cup Final |
| 1965 | Chicago | L | 4-3 | Semifinals |
| 1966 | Chicago | W | 4-2 | Semifinals |
| Montreal | L | 4-2 | Stanley Cup Final |
| 1970 | Chicago | L | 4-0 | Quarterfinals |
| 1978 | Atlanta | W | 2-0 | Preliminary Round |
| Montreal | L | 4-1 | Quarterfinals |
| 1984 | St. Louis | L | 3-1 | Norris Division Semifinals |
| 1985 | Chicago | L | 3-0 | Norris Division Semifinals |
| 1987 | Chicago | W | 4-0 | Norris Division Semifinals |
| Toronto | W | 4-3 | Norris Division Finals |
| Edmonton | L | 4-1 | Campbell Conference Final |
| 1988 | Toronto | W | 4-2 | Norris Division Semifinals |
| St. Louis | W | 4-1 | Norris Division Final |
| Edmonton | L | 4-1 | Campbell Conference Final |
| 1989 | Chicago | L | 4-2 | Norris Division Semifinals |
| 1991 | St. Louis | L | 4-3 | Norris Division Semifinals |
| 1992 | Dallas | W | 4-3 | Norris Division Semifinals |
| Chicago | L | 4-0 | Norris Division Finals |
| 1993 | Toronto | L | 4-3 | Norris Division Semifinals |
| 1994 | San Jose | L | 4-3 | Western Conference Quarterfinal |
| 1995 | Dallas | W | 4-1 | Western Conference Quarterfinal |
| San Jose | W | 4-0 | Western Conference Semifinal |
| Chicago | W | 4-1 | Western Conference Final |
| New Jersey | L | 4-0 | Stanley Cup Final |
| 1996 | Winnipeg | W | 4-2 | Western Conference Quarterfinal |
| St. Louis | W | 4-3 | Western Conference Semifinal |
| Colorado | L | 4-2 | Western Conference Final |
| 1997 | St. Louis | W | 4-2 | Western Conference Quarterfinal |
| Anaheim | W | 4-0 | Western Conference Semifinal |
| Colorado | W | 4-2 | Western Conference Final |
| Philadelphia | W | 4-0 | STANLEY CUP CHAMPIONS |
| 1998 | Phoenix | W | 4-2 | Western Conference Quarterfinal |
| St. Louis | W | 4-2 | Western Conference Semifinal |
| Dallas | W | 4-2 | Western Conference Final |
| Washington | W | 4-0 | STANLEY CUP CHAMPIONS |
| 1999 | Anahiem | W | 4-0 | Western Conference Quarterfinal |
| Colorado | L | 4-2 | Western Conference Semifinal |
| 2000 | Los Angeles | W | 4-0 | Western Conference Quarterfinal |
| Colorado | L | 4-1 | Western Conference Semifinal |
| 2001 | Los Angeles | L | 4-2 | Western Conference Quarterfinal |
| 2002 | Vancouver | W | 4-2 | Western Conference Quarterfinal |
| St. Louis | W | 4-1 | Western Conference Semifinal |
| Colorado | W | 4-3 | Western Conference Final |
| Carolina | W | 4-1 | STANLEY CUP CHAMPIONS |
| 2003 | Anaheim | L | 4-0 | Western Conference Quarterfinal |
| 2004 | Nashville | W | 4-2 | Western Conference Quarterfinal |
| Calgary | L | 4-2 | Western Conference Semifinal |
| 2006 | Edmonton | L | 4-2 | Western Conference Quarterfinal |
| 2007 | Calgary | W | 4-2 | Western Conference Quarterfinal |
| San Jose | W | 4-2 | Western Conference Semifinal |
| Anaheim | L | 4-2 | Western Conference Final |
| 2008 | Nashville | W | 4-2 | Western Conference Quarterfinal |
| Colorado | W | 4-0 | Western Conference Semifinal |
| Dallas | W | 4-2 | Western Conference Final |
| Pittsburgh | W | 4-2 | STANLEY CUP CHAMPIONS |
| 2009 | Columbus | W | 4-0 | Western Conference Quarterfinal |
| Anaheim | W | 4-3 | Western Conference Semifinal |
| Chicago | W | 4-1 | Western Conference Final |
| Pittsburgh | L | 4-3 | Stanley Cup Final |
| 2010 | Phoenix | W | 4-3 | Western Conference Quarterfinal |
| San Jose | L | 4-1 | Western Conference Semifinal |
| 2011 | Phoenix | W | 4-0 | Western Conference Quarterfinal |
| San Jose | L | 4-3 | Western Conference Semifinal |
| 2012 | Nashville | L | 4-1 | Western Conference Quarterfinal |
| 2013 | Anaheim | W | 4-3 | Western Conference Quarterfinal |
| Chicago | L | 4-3 | Western Conference Semifinal |
