| 1927 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-29 | Boston | L 1-6 |
| 3-31 | at Boston | T 4-4 |
| Boston won total-goals series 10-5 | ||
| 1930 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-23 | Montreal | L 0-1 |
| 3-26 | at Montreal | T 2-2 |
| Montreal won total-goals series 3-2 | ||
| 1931 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-24 | at Toronto | T 2-2 |
| 3-26 | Toronto | W 2-1 |
| Chicago won total-goals series 4-3 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-29 | NY Rangers | W 2-0 |
| 3-31 | at NY Rangers | W 1-0 |
| Chicago won total-goals series 3-0 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-3 | Montreal | L 1-2 |
| 4-5 | Montreal | W 2-1 |
| 4-9 | at Montreal | W 3-2 |
| 4-11 | at Montreal | L 2-4 |
| 4-14 | at Montreal | L 0-2 |
| Montreal won best-of-5 series 3-2 | ||
| 1932 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-27 | Toronto | W 1-0 |
| 3-29 | at Toronto | L 1-6 |
| Toronto won total-goals series 6-2 | ||
| 1934 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-22 | at Montreal | W 3-2 |
| 3-25 | Montreal | T 1-1 |
| Chicago won total-goals series 4-3 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-28 | at Mtl. Maroons | W 3-0 |
| 4-1 | Mtl. Maroons | W 3-2 |
| Chicago won total-goals series 6-2 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-3 | at Detroit | L 1-2 |
| 4-5 | at Detroit | W 2-1 |
| 4-8 | Detroit | W 3-2 |
| 4-10 | Detroit | L 2-4 |
| Chicago won best-of-5 series 3-1 | ||
| 1935 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-23 | at Mtl. Maroons | T 0-0 |
| 3-26 | Mtl. Maroons | L 0-1 |
| Maroons won total-goals series 1-0 | ||
| 1936 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-24 | at NY Americans | L 0-3 |
| 3-26 | NY Americans | W 5-4 |
| Americans won total-goals series 7-5 | ||
| 1938 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-22 | at Montreal | L 4-6 |
| 3-24 | Montreal | W 4-0 |
| 3-26 | at Montreal | W 3-2 |
| Chicago won best-of-3 series 2-1 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-29 | at NY Americans | L 1-3 |
| 3-31 | NY Americans | W 1-0 |
| 4-3 | at NY Americans | W 3-2 |
| Chicago won best-of-3 series 2-1 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-5 | at Toronto | W 3-1 |
| 4-7 | at Toronto | L 1-5 |
| 4-10 | Toronto | W 2-1 |
| 4-12 | Toronto | W 4-1 |
| Chicago won best-of-5 series 3-1 | ||
| 1940 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-19 | at Toronto | L 2-3 |
| 3-21 | Toronto | L 1-2 |
| Toronto won Best-of-3 series 2-0 | ||
| 1941 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-20 | Montreal | W 2-1 |
| 3-22 | at Montreal | L 3-4 |
| 3-25 | Montreal | W 3-2 |
| Chicago won best-of-3 series 2-1 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-27 | at Detroit | L 1-3 |
| 3-30 | Detroit | L 1-2 |
| Detroit won best-of-3 series 2-0 | ||
| 1942 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 3-22 | Boston | L 1-2 |
| 3-24 | at Boston | W 4-0 |
| 3-26 | at Boston | L 2-3 |
| Boston won best-of-3 series 2-1 | ||
| 1944 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-21 | at Detroit | W 2-1 |
| 3-23 | at Detroit | L 1-4 |
| 3-26 | Detroit | W 2-0 |
| 3-28 | Detroit | W 7-1 |
| 3-30 | at Detroit | W 5-2 |
| Chicago won best-of-7 series 4-1 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-4 | at Montreal | L 1-5 |
| 4-6 | Montreal | L 1-3 |
| 4-9 | Montreal | L 2-3 |
| 4-13 | at Montreal | L 4-5 |
| Montreal won best-of-7 series 4-0 | ||
| 1946 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-19 | at Montreal | L 2-6 |
| 3-21 | at Montreal | L 1-5 |
| 3-24 | Montreal | L 2-8 |
| 3-26 | Montreal | L 2-7 |
| Montreal won best-of-7 series 4-0 | ||
| 1953 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-24 | at Montreal | L 1-3 |
| 3-26 | at Montreal | L 3-4 |
| 3-29 | Montreal | W 2-1 |
| 3-31 | Montreal | W 3-1 |
| 4-2 | at Montreal | W 4-2 |
| 4-4 | Montreal | L 0-3 |
| 4-7 | at Montreal | L 1-4 |
| Montreal won best-of-7 series 4-3 | ||
| 1959 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-24 | at Montreal | L 2-4 |
| 3-26 | at Montreal | L 1-5 |
| 3-28 | Montreal | W 4-2 |
| 3-31 | Montreal | W 3-1 |
| 4-2 | at Montreal | L 2-4 |
| 4-4 | Montreal | L 4-5 |
| Montreal won best-of-7 series 4-2 | ||
| 1960 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-24 | at Montreal | L 3-4 |
| 3-26 | at Montreal | L 3-4 |
| 3-29 | Montreal | L 0-4 |
| 3-31 | Montreal | L 0-2 |
| Montreal won best-of-7 series 4-0 | ||
| 1961 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-21 | at Montreal | L 2-6 |
| 3-23 | at Montreal | W 4-3 |
| 3-26 | Montreal | W 2-1 |
| 3-28 | Montreal | L 2-5 |
| 4-1 | at Montreal | W 3-0 |
| 4-4 | Montreal | W 3-0 |
| Chicago won best-of-7 series 4-2 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-6 | Detroit | W 3-2 |
| 4-8 | at Detroit | L 1-3 |
| 4-10 | Detroit | W 3-1 |
| 4-12 | at Detroit | L 1-2 |
| 4-14 | Detroit | W 6-3 |
| 4-16 | at Detroit | W 5-1 |
| Chicago won best-of-7 series 4-2 | ||
| 1962 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-22 | at Montreal | L 1-2 |
| 3-22 | at Montreal | L 3-4 |
| 3-20 | Montreal | W 4-1 |
| 3-25 | Montreal | W 5-3 |
| 3-22 | at Montreal | W 4-3 |
| 3-20 | Montreal | W 2-0 |
| Chicago won best-of-7 series 4-2 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-10 | at Toronto | L 1-4 |
| 4-12 | at Toronto | L 2-3 |
| 4-15 | Toronto | W 3-0 |
| 4-17 | Toronto | W 4-1 |
| 4-19 | at Toronto | L 4-8 |
| 4-22 | Toronto | L 1-2 |
| Toronto won best-of-7 series 4-2 | ||
| 1963 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-26 | Detroit | W 5-4 |
| 3-28 | Detroit | W 5-2 |
| 3-31 | at Detroit | L 2-4 |
| 4-2 | at Detroit | L 1-4 |
| 4-4 | Detroit | L 2-4 |
| 4-7 | at Detroit | L 4-7 |
| Detroit won best-of-7 series 4-2 | ||
| 1964 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 3-26 | Detroit | W 4-1 |
| 3-29 | Detroit | L 4-5 |
| 3-31 | at Detroit | L 0-3 |
| 4-2 | at Detroit | W 3-2 |
| 4-5 | Detroit | W 3-2 |
| 4-7 | at Detroit | L 2-7 |
| 4-9 | Detroit | L 2-4 |
| Detroit won best-of-7 series 4-3 | ||
| 1965 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-1 | Detroit | L 3-4 |
| 4-4 | Detroit | L 3-6 |
| 4-6 | at Detroit | W 5-2 |
| 4-8 | at Detroit | W 2-1 |
| 4-11 | Detroit | L 2-4 |
| 4-13 | at Detroit | W 4-0 |
| 4-15 | Detroit | W 4-2 |
| Chicago won best-of-7 series 4-3 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-17 | at Montreal | L 2-3 |
| 4-20 | at Montreal | L 0-2 |
| 4-22 | Montreal | W 3-1 |
| 4-25 | Montreal | W 5-1 |
| 4-27 | at Montreal | L 0-6 |
| 4-29 | Montreal | W 2-1 |
| 5-1 | at Montreal | L 0-4 |
| Montreal won best-of-7 series 4-3 | ||
| 1966 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-7 | Detroit | W 2-1 |
| 4-10 | Detroit | L 0-7 |
| 4-12 | at Detroit | W 2-1 |
| 4-14 | at Detroit | L 1-5 |
| 4-17 | Detroit | L 3-5 |
| 4-19 | at Detroit | L 2-3 |
| Detroit won best-of-7 series 4-2 | ||
| 1967 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-6 | Toronto | W 5-2 |
| 4-9 | Toronto | L 1-3 |
| 4-11 | at Toronto | L 1-3 |
| 4-13 | at Toronto | W 4-3 |
| 4-15 | Toronto | L 2-4 |
| 4-18 | at Toronto | L 1-3 |
| Toronto won best-of-7 series 4-2 | ||
| 1968 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-4 | at NY Rangers | L 1-3 |
| 4-9 | at NY Rangers | L 1-2 |
| 4-11 | NY Rangers | W 7-4 |
| 4-13 | NY Rangers | W 3-1 |
| 4-14 | at NY Rangers | W 2-1 |
| 4-16 | NY Rangers | W 4-1 |
| Chicago won best-of-7 series 4-2 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-10 | at Montreal | L 2-9 |
| 4-20 | at Montreal | L 1-4 |
| 4-23 | Montreal | L 2-4 |
| 4-25 | Montreal | W 2-1 |
| 4-28 | at Montreal | L 3-4 |
| Montreal won best-of-7 series 4-1 | ||
| 1970 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-8 | Detroit | W 4-2 |
| 4-9 | Detroit | W 4-2 |
| 4-11 | at Detroit | W 4-2 |
| 4-12 | at Detroit | W 4-2 |
| Chicago won best-of-7 series 4-0 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-19 | Boston | L 3-6 |
| 4-21 | Boston | L 1-4 |
| 4-23 | at Boston | L 2-5 |
| 4-26 | at Boston | L 4-5 |
| Boston won best-of-7 series 4-0 | ||
| 1971 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-7 | Philadelphia | W 5-2 |
| 4-8 | Philadelphia | W 6-2 |
| 4-10 | at Philadelphia | W 3-2 |
| 4-11 | at Philadelphia | W 6-2 |
| Chicago won best-of-7 series 4-0 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-18 | NY Rangers | L 1-2 |
| 4-20 | NY Rangers | W 3-0 |
| 4-22 | at NY Rangers | L 1-4 |
| 4-25 | at NY Rangers | W 7-1 |
| 4-27 | NY Rangers | W 3-2 |
| 4-29 | at NY Rangers | L 2-3 |
| 5-2 | NY Rangers | W 4-2 |
| Chicago won best-of-7 series 4-3 | ||
| Finals | ||
| Date | Opponent | Result |
| 5-4 | Montreal | W 2-1 |
| 5-6 | Montreal | W 5-3 |
| 5-9 | at Montreal | L 2-4 |
| 5-11 | at Montreal | L 2-5 |
| 5-13 | Montreal | W 2-0 |
| 5-16 | at Montreal | L 3-4 |
| 5-18 | Montreal | L 2-3 |
| Montreal won best-of-7 series 4-3 | ||
| 1972 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-5 | Pittsburgh | W 3-1 |
| 4-6 | Pittsburgh | W 3-2 |
| 4-8 | at Pittsburgh | W 2-0 |
| 4-9 | at Pittsburgh | W 6-5 |
| Chicago won best-of-7 series 4-0 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-16 | NY Rangers | L 2-3 |
| 4-18 | NY Rangers | L 3-5 |
| 4-20 | at NY Rangers | L 2-3 |
| 4-23 | at NY Rangers | L 2-6 |
| NY Rangers won best-of-7 series 4-0 | ||
| 1973 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-4 | St. Louis | W 7-1 |
| 4-5 | St. Louis | W 1-0 |
| 4-7 | at St. Louis | W 5-2 |
| 4-8 | at St. Louis | L 3-5 |
| 4-10 | St. Louis | W 6-1 |
| Chicago won best-of-7 series 4-1 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-12 | NY Rangers | L 1-4 |
| 4-15 | NY Rangers | W 5-4 |
| 4-17 | at NY Rangers | W 2-1 |
| 4-19 | at NY Rangers | W 3-1 |
| 4-24 | NY Rangers | W 4-1 |
| Chicago won best-of-7 series 4-1 | ||
| Finals | ||
| Date | Opponent | Result |
| 4-29 | at Montreal | L 3-8 |
| 5-1 | at Montreal | L 1-4 |
| 5-3 | Montreal | W 7-4 |
| 5-6 | Montreal | L 0-4 |
| 5-8 | at Montreal | W 8-7 |
| 5-10 | Montreal | L 4-6 |
| Montreal won best-of-7 series 4-2 | ||
| 1974 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-10 | Los Angeles | W 3-1 |
| 4-11 | Los Angeles | W 4-1 |
| 4-13 | at Los Angeles | W 1-0 |
| 4-14 | at Los Angeles | L 1-5 |
| 4-16 | Los Angeles | W 1-0 |
| Chicago won best-of-7 series 4-1 | ||
| Semi-finals | ||
| Date | Opponent | Result |
| 4-18 | at Boston | W 4-2 |
| 4-21 | at Boston | L 6-8 |
| 4-23 | Boston | W 4-3 |
| 4-25 | Boston | L 2-5 |
| 4-28 | at Boston | L 2-6 |
| 4-30 | Boston | L 2-4 |
| Boston won best-of-7 series 4-2 | ||
| 1975 | ||
| Preliminary Round | ||
| Date | Opponent | Result |
| 4-8 | at Boston | L 2-8 |
| 4-10 | Boston | W 4-3 |
| 4-11 | at Boston | W 6-4 |
| Chicago won best-of-3 series 2-1 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-13 | at Buffalo | L 1-4 |
| 4-15 | at Buffalo | L 1-3 |
| 4-17 | Buffalo | W 5-4 |
| 4-20 | Buffalo | L 2-6 |
| 4-22 | at Buffalo | L 1-3 |
| Buffalo won best-of-7 series 4-1 | ||
| 1976 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-11 | at Montreal | L 0-4 |
| 4-13 | at Montreal | L 1-3 |
| 4-15 | Montreal | W 1-2 |
| 4-18 | Montreal | L 1-4 |
| Montreal won best-of-7 series 4-0 | ||
| 1977 | ||
| Preliminary Round | ||
| Date | Opponent | Result |
| 4-5 | at NY Islanders | L 2-5 |
| 4-7 | NY Islanders | L 1-2 |
| NY Islanders won best-of-3 series 2-0 | ||
| 1978 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-17 | at Boston | L 1-6 |
| 4-19 | at Boston | L 3-4 |
| 4-21 | Boston | L 3-4 |
| 4-23 | Boston | L 2-5 |
| Boston won best-of-7 series 4-0 | ||
| 1979 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-16 | at NY Islanders | L 2-6 |
| 4-18 | at NY Islanders | L 0-1 |
| 4-20 | NY Islanders | L 0-4 |
| 4-22 | NY Islanders | L 1-3 |
| NY Islanders won best-of-7 series 4-0 | ||
| 1980 | ||
| Preliminary Round | ||
| Date | Opponent | Result |
| 4-8 | St. Louis | W 3-2 |
| 4-9 | St. Louis | W 5-1 |
| 4-11 | at St. Louis | W 4-1 |
| Chicago won best-of-5 series 3-0 | ||
| Quarter-finals | ||
| Date | Opponent | Result |
| 4-16 | at Buffalo | L 0-5 |
| 4-17 | at Buffalo | L 4-6 |
| 4-19 | Buffalo | L 1-2 |
| 4-20 | Buffalo | L 2-3 |
| Buffalo won best-of-7 series 4-0 | ||
| 1981 | ||
| Preliminary Round | ||
| Date | Opponent | Result |
| 4-8 | at Calgary | L 3-4 |
| 4-9 | at Calgary | L 2-6 |
| 4-11 | Calgary | L 4-5 |
| Calgary won best-of-5 series 3-0 | ||
| 1982 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-7 | at Minnesota | W 3-2 |
| 4-8 | at Minnesota | W 5-3 |
| 4-10 | Minnesota | L 1-7 |
| 4-11 | Minnesota | W 5-2 |
| Chicago won best-of-5 series 3-1 | ||
| Division Finals | ||
| Date | Opponent | Result |
| 4-15 | at St. Louis | W 5-4 |
| 4-16 | at St. Louis | L 1-3 |
| 4-18 | St. Louis | W 6-5 |
| 4-19 | St. Louis | W 7-4 |
| 4-21 | at St. Louis | L 2-3 |
| 4-23 | St. Louis | W 2-0 |
| Chicago won best-of-7 series 4-2 | ||
| Conference Finals | ||
| Date | Opponent | Result |
| 4-27 | Vancouver | L 1-2 |
| 4-29 | Vancouver | W 4-1 |
| 5-1 | at Vancouver | L 3-4 |
| 5-4 | at Vancouver | L 3-5 |
| 5-6 | Vancouver | L 2-6 |
| Vancouver won best-of-7 series 4-1 | ||
| 1983 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-6 | St. Louis | L 2-4 |
| 4-7 | St. Louis | W 7-2 |
| 4-9 | at St. Louis | W 2-1 |
| 4-10 | at St. Louis | W 5-3 |
| Chicago won best-of-5 series 3-1 | ||
| Division Finals | ||
| Date | Opponent | Result |
| 4-14 | Minnesota | W 5-2 |
| 4-15 | Minnesota | W 7-4 |
| 4-17 | at Minnesota | L 1-5 |
| 4-18 | at Minnesota | W 4-3 |
| 4-20 | Minnesota | W 5-2 |
| Chicago won best-of-7 series 4-1 | ||
| Conference Finals | ||
| Date | Opponent | Result |
| 4-24 | at Edmonton | L 4-8 |
| 4-26 | at Edmonton | L 2-8 |
| 5-1 | Edmonton | L 2-3 |
| 5-3 | Edmonton | L 3-6 |
| Edmonton won best-of-7 series 4-0 | ||
| 1984 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-4 | at Minnesota | W 3-1 |
| 4-5 | at Minnesota | L 5-6 |
| 4-7 | Minnesota | L 1-4 |
| 4-8 | Minnesota | W 4-3 |
| 4-10 | at Minnesota | L 1-4 |
| Minnesota won best-of-5 series 3-2 | ||
| 1985 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-10 | Detroit | W 9-5 |
| 4-11 | Detroit | W 6-1 |
| 4-13 | at Detroit | W 8-2 |
| Chicago won best-of-5 series 3-0 | ||
| Division Finals | ||
| Date | Opponent | Result |
| 4-18 | Minnesota | L 5-8 |
| 4-21 | Minnesota | W 6-2 |
| 4-23 | at Minnesota | W 5-3 |
| 4-25 | at Minnesota | W 7-6 |
| 4-28 | Minnesota | L 4-5 |
| 4-30 | at Minnesota | W 6-5 |
| Chicago won best-of-7 series 4-2 | ||
| Conference Finals | ||
| Date | Opponent | Result |
| 5-4 | at Edmonton | L 2-11 |
| 5-7 | at Edmonton | L 3-7 |
| 5-9 | Edmonton | W 5-2 |
| 5-12 | Edmonton | W 8-6 |
| 5-14 | at Edmonton | L 5-10 |
| 5-16 | Edmonton | L 2-8 |
| Edmonton won best-of-7 series 4-2 | ||
| 1986 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-9 | Toronto | L 3-5 |
| 4-10 | Toronto | L 4-6 |
| 4-12 | at Toronto | L 2-7 |
| Toronto won best-of-5 series 3-0 | ||
| 1987 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-8 | at Detroit | L 1-3 |
| 4-9 | at Detroit | L 1-5 |
| 4-11 | Detroit | L 3-4 |
| 4-12 | Detroit | L 1-3 |
| Detroit won best-of-7 series 4-0 | ||
| 1988 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-6 | at St. Louis | L 1-4 |
| 4-7 | at St. Louis | L 2-3 |
| 4-9 | St. Louis | W 6-3 |
| 4-10 | St. Louis | L 5-6 |
| 4-12 | at St. Louis | L 3-5 |
| St. Louis won best-of-7 series 4-1 | ||
| 1989 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-5 | at Detroit | L 2-3 |
| 4-6 | at Detroit | W 5-4 |
| 4-8 | Detroit | W 4-2 |
| 4-9 | Detroit | W 3-2 |
| 4-11 | at Detroit | L 4-6 |
| 4-13 | Detroit | W 7-1 |
| Chicago won best-of-7 series 4-2 | ||
| Division Finals | ||
| Date | Opponent | Result |
| 4-18 | at St. Louis | W 3-1 |
| 4-20 | at St. Louis | L 4-5 |
| 4-22 | St. Louis | W 5-2 |
| 4-24 | St. Louis | W 3-2 |
| 4-26 | at St. Louis | W 4-2 |
| Chicago won best-of-7 series 4-1 | ||
| Conference Finals | ||
| Date | Opponent | Result |
| 5-2 | at Calgary | L 0-3 |
| 5-4 | at Calgary | W 4-2 |
| 5-6 | Calgary | L 2-5 |
| 5-8 | Calgary | L 1-2 |
| 5-10 | at Calgary | L 1-3 |
| Calgary won best-of-7 series 4-1 | ||
| 1990 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-4 | Minnesota | L 1-2 |
| 4-6 | Minnesota | W 5-3 |
| 4-8 | at Minnesota | W 2-1 |
| 4-10 | at Minnesota | L 0-4 |
| 4-12 | Minnesota | W 5-1 |
| 4-14 | at Minnesota | L 3-5 |
| 4-16 | Minnesota | W 5-2 |
| Chicago won best-of-7 series 4-3 | ||
| Division Finals | ||
| Date | Opponent | Result |
| 4-18 | St. Louis | L 3-4 |
| 4-20 | St. Louis | W 5-3 |
| 4-22 | at St. Louis | L 4-5 |
| 4-24 | at St. Louis | W 3-2 |
| 4-26 | St. Louis | W 3-2 |
| 4-28 | at St. Louis | L 2-4 |
| 4-30 | St. Louis | W 8-2 |
| Chicago won best-of-7 series 4-3 | ||
| Conference Finals | ||
| Date | Opponent | Result |
| 5-2 | at Edmonton | L 2-5 |
| 5-4 | at Edmonton | W 4-3 |
| 5-6 | Edmonton | W 5-1 |
| 5-8 | Edmonton | L 2-4 |
| 5-10 | at Edmonton | L 3-4 |
| 5-12 | Edmonton | L 4-8 |
| Edmonton won best-of-7 series 4-2 | ||
| 1991 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-4 | Minnesota | L 3-4 |
| 4-6 | Minnesota | W 5-2 |
| 4-8 | at Minnesota | W 6-5 |
| 4-10 | at Minnesota | L 1-3 |
| 4-12 | Minnesota | L 0-6 |
| 4-14 | at Minnesota | L 1-3 |
| Minnesota won best-of-7 series 4-2 | ||
| 1992 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-18 | St. Louis | W 3-1 |
| 4-20 | St. Louis | L 3-5 |
| 4-22 | at St. Louis | L 4-5 |
| 4-24 | at St. Louis | W 5-3 |
| 4-26 | St. Louis | W 6-4 |
| 4-28 | at St. Louis | W 2-1 |
| Chicago won best-of-7 series 4-2 | ||
| Division Finals | ||
| Date | Opponent | Result |
| 5-2 | at Detroit | W 2-1 |
| 5-4 | at Detroit | W 3-1 |
| 5-6 | Detroit | W 5-4 |
| 5-8 | Detroit | W 1-0 |
| Chicago won best-of-7 series 4-0 | ||
| Conference Finals | ||
| Date | Opponent | Result |
| 5-16 | Edmonton | W 8-2 |
| 5-18 | Edmonton | W 4-2 |
| 5-20 | at Edmonton | W 4-3 |
| 5-22 | at Edmonton | W 5-1 |
| Chicago won best-of-7 series 4-0 | ||
| Finals | ||
| Date | Opponent | Result |
| 5-26 | at Pittsburgh | L 4-5 |
| 5-28 | at Pittsburgh | L 1-3 |
| 5-30 | Pittsburgh | L 0-1 |
| 6-1 | Pittsburgh | L 5-6 |
| Pittsburgh won best-of-7 series 4-0 | ||
| 1993 | ||
| Division Semi-finals | ||
| Date | Opponent | Result |
| 4-18 | St. Louis | L 3-4 |
| 4-21 | St. Louis | L 0-2 |
| 4-23 | at St. Louis | L 0-3 |
| 4-25 | at St. Louis | L 3-4 |
| St. Louis won best-of-7 series 4-0 | ||
| 1994 | ||
| Conference Quarter-finals | ||
| Date | Opponent | Result |
| 4-18 | at Toronto | L 1-5 |
| 4-20 | at Toronto | L 0-1 |
| 4-23 | Toronto | W 5-4 |
| 4-24 | Toronto | W 4-3 |
| 4-26 | at Toronto | L 0-1 |
| 4-28 | Toronto | L 0-1 |
| Toronto won best-of-7 series 4-2 | ||
| 1995 | ||
| Conference Quarter-finals | ||
| Date | Opponent | Result |
| 5-7 | Toronto | L 3-5 |
| 5-9 | Toronto | L 0-3 |
| 5-11 | at Toronto | W 3-2 |
| 5-13 | at Toronto | W 3-1 |
| 5-15 | Toronto | W 4-2 |
| 5-17 | at Toronto | L 4-5 |
| 5-19 | Toronto | W 5-2 |
| Chicago won best-of-7 series 4-3 | ||
| Conference Semi-finals | ||
| Date | Opponent | Result |
| 5-21 | Vancouver | W 2-1 |
| 5-23 | Vancouver | W 2-0 |
| 5-25 | at Vancouver | W 3-2 |
| 5-27 | at Vancouver | W 4-3 |
| Chicago won best-of-7 series 4-0 | ||
| Conference Finals | ||
| Date | Opponent | Result |
| 6-1 | at Detroit | L 1-2 |
| 6-4 | at Detroit | L 2-3 |
| 6-6 | Detroit | L 3-4 |
| 6-8 | Detroit | W 5-2 |
| 6-11 | at Detroit | L 1-2 |
| Detroit won best-of-7 series 4-1 | ||
| 1996 | ||
| Conference Quarter-finals | ||
| Date | Opponent | Result |
| 4-17 | Calgary | W 4-1 |
| 4-19 | Calgary | W 3-0 |
| 4-21 | at Calgary | W 7-5 |
| 4-23 | at Calgary | W 2-1 |
| Chicago won best-of-7 series 4-0 | ||
| Conference Semi-finals | ||
| Date | Opponent | Result |
| 5-2 | at Colorado | W 3-2 |
| 5-4 | at Colorado | L 1-5 |
| 5-6 | Colorado | W 4-3 |
| 5-8 | Colorado | L 2-3 |
| 5-11 | at Colorado | L 1-4 |
| 5-13 | Colorado | L 3-4 |
| Colorado won best-of-7 series 4-2 | ||
| 1997 | ||
| Conference Quarter-finals | ||
| Date | Opponent | Result |
| 4-16 | at Colorado | L 0-6 |
| 4-18 | at Colorado | L 1-3 |
| 4-20 | Colorado | W 4-3 |
| 4-22 | Colorado | W 6-3 |
| 4-24 | at Colorado | L 0-7 |
| 4-26 | Colorado | L 3-6 |
| Colorado won best-of-7 series 4-2 | ||