| Sep 17, 1989 Sun | Preseason | St. Louis | Chicago | Dirk-Peluso Dirk-Van Dorp Momesso-Bassen |
| Sep 19, 1989 Tue | Preseason | Chicago | Minnesota | (Cheap) Secord-Tinordi Peluso-Robinson (5.7) |
| Sep 22, 1989 Fri | Preseason | Chicago | St. Louis | Van Dorp-Twist (7) (Rough) Savard-Oates |
| Sep 23, 1989 Sat | Preseason | Chicago | Edmonton | Eagles-Beukeboom Russell-Buchberger (7) (Rough) Manson-Simpson |
| Sep 24, 1989 Sun | Preseason | Buffalo | Chicago | Add Fight |
| Sep 27, 1989 Wed | Preseason | Chicago | Buffalo | Add Fight |
| Sep 28, 1989 Thu | Preseason | Minnesota | Chicago | Add Fight |
| Sep 30, 1989 Sat | Preseason | Chicago | Vancouver | Add Fight |
| Oct 1, 1989 Sun | Preseason | Edmonton | Chicago | Ware-Secord Brown-Peluso McClelland-McGill Ware-Manson |
| Oct 5, 1989 Thu | | St. Louis | Chicago | Raglan-Yawney (4) Twist-Van Dorp (5.4) Lalor-Murray (2) |
| Oct 7, 1989 Sat | | Chicago | Washington | Graham-May |
| Oct 8, 1989 Sun | | NY Rangers | Chicago | Ruff-Thomas Sandstrom-Presley Moller-Creighton Nilan-Secord (5.8) (Cheap) Nilan-Chevrier (4) Nilan-Manson (2.8) Abuse at 56:41 |
| Oct 12, 1989 Thu | | Toronto | Chicago | Add Fight |
| Oct 14, 1989 Sat | | Chicago | St. Louis | Hudson-Cavallini McGill-Brind'Amour (4) |
| Oct 15, 1989 Sun | | Detroit | Chicago | (Hit) Salming-Gilbert Gallant-Gilbert (1) |
| Oct 17, 1989 Tue | | Chicago | NY Rangers | Add Fight |
| Oct 19, 1989 Thu | | Quebec | Chicago | Add Fight |
| Oct 20, 1989 Fri | | Chicago | Winnipeg | Add Fight |
| Oct 22, 1989 Sun | | Los Angeles | Chicago | Add Fight |
| Oct 24, 1989 Tue | | Chicago | Detroit | Add Fight |
| Oct 26, 1989 Thu | | Montreal | Chicago | (Cheap) Richer-Manson |
| Oct 28, 1989 Sat | | Chicago | New Jersey | Add Fight |
| Oct 29, 1989 Sun | | Washington | Chicago | Hatcher-Sutter May-McGill |
| Oct 31, 1989 Tue | | Chicago | Quebec | (Hit) Thomas-Petit (Hit) Thomas-Lafleur Thomas-Hough Graham-McRae |
| Nov 2, 1989 Thu | | Minnesota | Chicago | Churla-Van Dorp (6.2) |
| Nov 4, 1989 Sat | | Chicago | Minnesota | (Almost) Yawney-Donatelli Sutter-Chambers (5) Yawney-Donatelli (8) (Cheap) Gilbert-Churla McGill-Churla (7.4) (Cheap) Creighton-Siren Creighton-Wilkinson (5) |
| Nov 5, 1989 Sun | | Winnipeg | Chicago | Cronin-Van Dorp (3.5) |
| Nov 9, 1989 Thu | | Pittsburgh | Chicago | Add Fight |
| Nov 11, 1989 Sat | | Chicago | NY Islanders | Thomas-Kerr Hudson-Pryor |
| Nov 12, 1989 Sun | | Hartford | Chicago | Add Fight |
| Nov 16, 1989 Thu | | Chicago | Vancouver | Add Fight |
| Nov 18, 1989 Sat | | Chicago | Calgary | Manson-Hunter (4) (Rough) Chevrier-Fleury (4) |
| Nov 19, 1989 Sun | | Chicago | Edmonton | Add Fight |
| Nov 22, 1989 Wed | | Chicago | Los Angeles | (Hit) Roenick-Benning (2) Van Dorp-Miller (4.5) Van Dorp-Kudelski (5) Manson-Crowder (5.8) |
| Nov 26, 1989 Sun | | Chicago | Minnesota | Add Fight |
| Nov 30, 1989 Thu | | NY Islanders | Chicago | Vukota-Secord (7.6) Scrum at 9:32 Scrum at 25:47 Crossman-Sutter |
| Dec 3, 1989 Sun | | Detroit | Chicago | (Rough) Shank-Eagles Robertson-Van Dorp Scrum at 9:57 McClelland-Eagles (6) Mokosak-Van Dorp Robertson-Sanipass Mokosak-Sanipass |
| Dec 6, 1989 Wed | | Toronto | Chicago | Richardson-Gilbert (3) (Cheap) McIntyre-Manson (6) |
| Dec 9, 1989 Sat | | Chicago | Pittsburgh | Add Fight |
| Dec 10, 1989 Sun | | Vancouver | Chicago | Add Fight |
| Dec 13, 1989 Wed | | Chicago | Montreal | Brown-McPhee (2) |
| Dec 15, 1989 Fri | | Chicago | Detroit | Van Dorp-Adams (0) |
| Dec 17, 1989 Sun | | Edmonton | Chicago | Add Fight |
| Dec 20, 1989 Wed | | St. Louis | Chicago | (Rough) Twist-Van Dorp (2) (Rough) Roberts-Yawney (3) Lalor-Eagles (3) (Rough) Zezel-Manson Chase-Van Dorp (5.4) Twist-Manson (3.7) |
| Dec 22, 1989 Fri | | Toronto | Chicago | McIntyre-Manson Curran-Van Dorp |
| Dec 23, 1989 Sat | | Chicago | Toronto | Hudson-Curran Murray-Fergus (5) Sutter-Franceschetti (2) Vincelette-Gill (3) Brawl at 20:00 (10) Graham-McIntyre Savard-Leeman (8) Russell-Curran (2.5) Manson-Leeman Abuse at 20:00 (10) Russell-Kordic (7.8) Sutter-Iafrate (3) |
| Dec 26, 1989 Tue | | Chicago | St. Louis | Sutter-Cavallini Van Dorp-Twist (1.2) |
| Dec 28, 1989 Thu | | Minnesota | Chicago | Churla-Van Dorp (8.2) Bench-Clearing Brawl at 0:00 (10) (Rough) Churla-Van Dorp (Almost) Wilkinson-Peluso (Almost) Wilkinson-Graham (2) (Rough) Bellows-Sutter (2) Mini-Brawl at 4:01 (5) McRae-Secord (5.7) Gavin-Sutter Mini-Brawl at 36:04 McRae-Peluso (7.2) (Hit) Murphy-Roenick (2) |
| Dec 30, 1989 Sat | | Hartford | Chicago | (Rough) Jennings-McGill Mini-Brawl at 37:45 |
| Jan 3, 1990 Wed | | Edmonton | Chicago | Graves-Sutter (5) Brown-Russell (8.3) Beukeboom-Roenick (2) |
| Jan 6, 1990 Sat | | Philadelphia | Chicago | Tocchet-McGill (2) |
| Jan 10, 1990 Wed | | Chicago | NY Rangers | Scrum at 19:13 (Cheap) Roenick-King McGill-King (5.3) |
| Jan 11, 1990 Thu | | Chicago | Philadelphia | Scrum at 28:39 (3) Graham-Berube (3.8) |
| Jan 14, 1990 Sun | | Calgary | Chicago | Add Fight |
| Jan 15, 1990 Mon | | Chicago | Toronto | Creighton-Curran (3) Russell-Kordic (6.8) (Hit) Roenick-Pearson (5) (Rough) McGill-Pearson |
| Jan 17, 1990 Wed | | Minnesota | Chicago | Add Fight |
| Jan 19, 1990 Fri | | Vancouver | Chicago | Stern-McGill |
| Jan 24, 1990 Wed | | Buffalo | Chicago | Add Fight |
| Jan 26, 1990 Fri | | Chicago | Buffalo | Add Fight |
| Jan 27, 1990 Sat | | Chicago | Hartford | (Rough) Murray-Quenneville (Rough) Creighton-Verbeek Graham-Samuelsson |
| Feb 1, 1990 Thu | | Chicago | Los Angeles | Creighton-Miller (4) (Hit) Roenick-McSorley (2) Roenick-McSorley (3.8) |
| Feb 4, 1990 Sun | | Chicago | Winnipeg | Add Fight |
| Feb 8, 1990 Thu | | Chicago | Detroit | (Hit) Thomas-Burr Hudson-McClelland (4) Manson-Kocur (1.5) McGill-Kocur (1) (Rough) Graham-Shank (4) |
| Feb 10, 1990 Sat | | Chicago | Minnesota | (Almost) McGill-McRae (Almost) McGill-McRae Lemieux-Wilkinson (9) |
| Feb 13, 1990 Tue | | Buffalo | Chicago | Hartman-McGill (6) |
| Feb 15, 1990 Thu | | Calgary | Chicago | (Cheap) MacLellan-McGill (4) Hunter-Van Dorp (3) Murzyn-Sutter (3) |
| Feb 17, 1990 Sat | | Chicago | NY Islanders | (Hit) Cloutier-Vukota (Rough) Manson-Vukota (1) Murray-Nylund (2) McGill-Kerr (5) Sutter-Baumgartner (6) Creighton-Bergevin (5) |
| Feb 18, 1990 Sun | | Pittsburgh | Chicago | (Cheap) Pederson-Van Dorp (3) Buskas-Van Dorp (2) Cullen-Presley (5) Brawl at 57:23 |
| Feb 20, 1990 Tue | | Chicago | St. Louis | Add Fight |
| Feb 22, 1990 Thu | | Boston | Chicago | (Cheap) Bourque-Sutter Pedersen-Sutter (4) |
| Feb 24, 1990 Sat | | Chicago | New Jersey | Add Fight |
| Feb 25, 1990 Sun | | Philadelphia | Chicago | Carkner-Van Dorp (4) Tocchet-Brown (2) Berube-Konroyd Brawl at 18:22 (Rough) Wells-Thomas Berube-Roenick (5) |
| Feb 27, 1990 Tue | | Chicago | Washington | Graham-Stevens (5.3) Manson-Stevens (4.3) |
| Mar 1, 1990 Thu | | St. Louis | Chicago | Dirk-Hudson (6) Lalor-Sutter (5) Momesso-Van Dorp (5) Scrum at 19:56 (3) |
| Mar 3, 1990 Sat | | Chicago | Boston | (Hit) Thomas-Carpenter (2) (Hit) Gilbert-Galley (2) (Hit) Van Dorp-Bourque Sutter-Gould (3) |
| Mar 4, 1990 Sun | | Boston | Chicago | (Hit) Sweeney-Murray (2) Collision (3) (Hit) Bourque-Gilbert Douris-Sutter (4) Byers-Van Dorp (5.7) Sweeney-McGill (3) Scrum at 46:12 (2) Byers-Van Dorp (7) |
| Mar 7, 1990 Wed | | Chicago | Minnesota | Gilbert-Churla (1) Manson-McRae (1) (Cheap) Murray-unknown |
| Mar 10, 1990 Sat | | Chicago | St. Louis | Creighton-Momesso (5) Van Dorp-Chase (5) Goulet-Sutter |
| Mar 11, 1990 Sun | | St. Louis | Chicago | (Hit) Featherstone-Goulet (4) Chase-McGill |
| Mar 13, 1990 Tue | | Detroit | Chicago | (Rough) McClelland-Van Dorp (0) McKay-Secord (6) |
| Mar 15, 1990 Thu | | Chicago | Quebec | (Hit) Van Dorp-Fortier |
| Mar 17, 1990 Sat | | Chicago | Montreal | Van Dorp-Ewen (3) |
| Mar 19, 1990 Mon | | Chicago | Toronto | (Rough) Yawney-Marois (Rough) McGill-Daoust |
| Mar 22, 1990 Thu | | New Jersey | Chicago | Maley-Creighton |
| Mar 24, 1990 Sat | | Chicago | Detroit | Event McGill-Probert (6) Lemieux-McKay (6.3) Brown-Gallant (3) |
| Mar 25, 1990 Sun | | Detroit | Chicago | Probert-Manson (3.3) Probert-Van Dorp (4.8) McClelland-McGill (8) Zombo-Lemieux (8) McKay-Secord (5) |
| Mar 29, 1990 Thu | | Toronto | Chicago | (Almost) Kordic-McGill (Almost) Curran-Secord (Cheap) Marsh-Savard Brawl at 53:22 (8) Hannan-Manson (6) Pearson-McGill (4) |
| Mar 31, 1990 Sat | | Chicago | Toronto | Van Dorp-Kordic (6) (Rough) Creighton-Leeman |
| Apr 1, 1990 Sun | | Minnesota | Chicago | Scrum at 4:07 Churla-Manson (2.5) McRae-Secord (Cheap) unknown-Van Dorp Mini-Brawl at 46:02 Tinordi-Presley (5.7) Tinordi-Presley (3) McRae-Manson (6.7) Wilkinson-Secord (3) |
| Apr 4, 1990 Wed | Round 1 | Game 1 | Minnesota | Chicago | Add Fight |
| Apr 6, 1990 Fri | Round 1 | Game 2 | Minnesota | Chicago | (Rough) Murphy-Presley (Rough) Broten-Yawney (Rough) McRae-Roenick (Rough) Musil-Roenick Wilkinson-Creighton (5) Scrum at 30:23 Scrum at 32:55 (Rough) Dahlen-Yawney (Rough) Bellows-Savard (Cheap) Murphy-unknown |
| Apr 8, 1990 Sun | Round 1 | Game 3 | Chicago | Minnesota | Gilbert-Chambers (4) Scrum at 28:07 (Rough) Sutter-Barber |
| Apr 10, 1990 Tue | Round 1 | Game 4 | Chicago | Minnesota | Mini-Brawl at 38:03 Konroyd-Churla (7.5) (Rough) Van Dorp-Churla |
| Apr 12, 1990 Thu | Round 1 | Game 5 | Minnesota | Chicago | Churla-Van Dorp (2) |
| Apr 14, 1990 Sat | Round 1 | Game 6 | Chicago | Minnesota | Add Fight |
| Apr 16, 1990 Mon | Round 1 | Game 7 | Minnesota | Chicago | Add Fight |
| Apr 18, 1990 Wed | QF | Game 1 | St. Louis | Chicago | Lalor-Presley (5) |
| Apr 20, 1990 Fri | QF | Game 2 | St. Louis | Chicago | Add Fight |
| Apr 22, 1990 Sun | QF | Game 3 | Chicago | St. Louis | Add Fight |
| Apr 24, 1990 Tue | QF | Game 4 | Chicago | St. Louis | Sutter-Chase (5.3) (Cheap) unknown-Hull |
| Apr 26, 1990 Thu | QF | Game 5 | St. Louis | Chicago | Lowry-Yawney (6) (Cheap) unknown-Thomas |
| Apr 28, 1990 Sat | QF | Game 6 | Chicago | St. Louis | Lemieux-Snepsts (7.8) Gilbert-Sutter (Cheap) unknown-Snepsts |
| Apr 30, 1990 Mon | QF | Game 7 | St. Louis | Chicago | Featherstone-Gilbert (3) (Cheap) Momesso-unknown |
| May 2, 1990 Wed | SF | Game 1 | Chicago | Edmonton | Add Fight |
| May 4, 1990 Fri | SF | Game 2 | Chicago | Edmonton | Add Fight |
| May 6, 1990 Sun | SF | Game 3 | Edmonton | Chicago | (Rough) Huddy-Gilbert |
| May 8, 1990 Tue | SF | Game 4 | Edmonton | Chicago | (Rough) Murphy-Konroyd (Rough) Kurri-Savard (Cheap) Ranford-Lemieux |
| May 10, 1990 Thu | SF | Game 5 | Chicago | Edmonton | Add Fight |
| May 12, 1990 Sat | SF | Game 6 | Edmonton | Chicago | Add Fight |