| Sep 18, 1988 Sun | Preseason | Detroit | Chicago | King-Playfair Event |
| Sep 23, 1988 Fri | Preseason | Chicago | Edmonton | Manson-Muni Brown-Lacombe Manson-Beukeboom Cochrane-McClelland (Rough) Vincelette-Buchberger |
| Sep 24, 1988 Sat | Preseason | Chicago | St. Louis | Mackey-Ewen McGill-Ewen Graham-Evans Vincelette-Ewen |
| Sep 25, 1988 Sun | Preseason | Minnesota | Chicago | Gaetz-Mackey (6) Zemlak-Cochrane Kolstad-Mackey Rouse-Vincelette McHugh-Sutter (6) |
| Sep 27, 1988 Tue | Preseason | Chicago | Minnesota | Bergevin-Babe Manson-Robinson |
| Sep 28, 1988 Wed | Preseason | Chicago | Minnesota | Cochrane-Zemlak Sutter-Lawton Nylund-Zemlak Playfair-Kolstad |
| Oct 1, 1988 Sat | Preseason | Edmonton | Chicago | Add Fight |
| Oct 2, 1988 Sun | Preseason | St. Louis | Chicago | Add Fight |
| Oct 6, 1988 Thu | | NY Rangers | Chicago | Nilan-Cochrane (3) Granato-Yawney (3.5) |
| Oct 8, 1988 Sat | | Chicago | Toronto | Add Fight |
| Oct 9, 1988 Sun | | Toronto | Chicago | Curran-Manson Secord-Cochrane Osborne-Thomas Laxdal-Sutter |
| Oct 12, 1988 Wed | | Winnipeg | Chicago | Marois-McGill |
| Oct 15, 1988 Sat | | Chicago | Hartford | Playfair-Jennings (3) |
| Oct 16, 1988 Sun | | Boston | Chicago | (Rough) Neely-Manson Galley-Playfair |
| Oct 18, 1988 Tue | | Chicago | Detroit | Thomas-King (7) Mini-Brawl at 26:30 (6) Playfair-Zombo (7) Manson-Barr (2) Yawney-Graves (5) |
| Oct 20, 1988 Thu | | Chicago | St. Louis | McGill-Cavallini (3) Vincelette-Dirk (6) (Rough) Vaive-Richter |
| Oct 22, 1988 Sat | | Chicago | Pittsburgh | Nylund-Hillier (3) Manson-Frawley (4.7) (Almost) Sutter-Hillier (Rough) Nylund-Quinn Mini-Brawl at 59:17 Playfair-Dykstra (5) (Almost) McGill-Kachowski |
| Oct 25, 1988 Tue | | Chicago | Quebec | Nylund-Gillis |
| Oct 28, 1988 Fri | | Chicago | Vancouver | Thomas-Lidster (5) Brawl at 60:00 Manson-Bruce (5) |
| Oct 30, 1988 Sun | | Chicago | Edmonton | Vincelette-Beukeboom |
| Oct 31, 1988 Mon | | Chicago | Calgary | (Rough) Vaive-Berezan |
| Nov 3, 1988 Thu | | Minnesota | Chicago | Add Fight |
| Nov 5, 1988 Sat | | Chicago | Minnesota | Add Fight |
| Nov 6, 1988 Sun | | Los Angeles | Chicago | Crossman-Ludzik |
| Nov 9, 1988 Wed | | Montreal | Chicago | Corson-Brown (3.5) Svoboda-Presley (2) |
| Nov 11, 1988 Fri | | Chicago | Winnipeg | Add Fight |
| Nov 13, 1988 Sun | | Quebec | Chicago | Add Fight |
| Nov 16, 1988 Wed | | Buffalo | Chicago | Add Fight |
| Nov 19, 1988 Sat | | Chicago | Montreal | (Hit) Savard-Ludwig (Cheap) Roenick-Chelios (Hit) Wilson-Gainey (Cheap) Yawney-Ludwig (7) |
| Nov 20, 1988 Sun | | Vancouver | Chicago | Butcher-Vincelette (5) |
| Nov 23, 1988 Wed | | Chicago | Toronto | McGill-Kordic (8) |
| Nov 25, 1988 Fri | | Chicago | Buffalo | McGill-Hartman (6) |
| Nov 26, 1988 Sat | | Chicago | Boston | (Rough) Manson-Neely Sutter-Byers (2.8) McGill-Miller (6.2) Sanipass-Byers (7.7) (Rough) Manson-Miller |
| Nov 29, 1988 Tue | | Chicago | Minnesota | Sutter-Hartsburg (6.5) Mini-Brawl at 34:04 (7) Sutter-Hardy (5) Vincelette-Bellows (7) Sanipass-Rouse (1) |
| Dec 3, 1988 Sat | | Chicago | Los Angeles | Add Fight |
| Dec 6, 1988 Tue | | Chicago | Pittsburgh | (Cheap) Vincelette-Cunneyworth (3) Mini-Brawl (3) Sanipass-Caufield (2.5) |
| Dec 10, 1988 Sat | | Chicago | Philadelphia | (Cheap) unknown-Kerr (Rough) Sutter-Mellanby (Cheap) unknown-Tocchet Scrum at 59:55 |
| Dec 11, 1988 Sun | | St. Louis | Chicago | Raglan-McGill (2) Cavallini-Sutter (2) Benning-Thomas (3) (Rough) Evans-McGill Mini-Brawl at 57:34 Coxe-Manson (2.5) Richter-Sanipass (6.4) |
| Dec 14, 1988 Wed | | Hartford | Chicago | (Rough) Jennings-Sutter Mini-Brawl at 35:43 Martin-Manson (3) Jennings-Sanipass (2) (Cheap) Martin-Presley (4) Martin-Murray (1) |
| Dec 17, 1988 Sat | | Chicago | St. Louis | Brown-Cavallini Mini-Brawl at 50:04 McGill-Momesso Thomas-Vesey |
| Dec 18, 1988 Sun | | New Jersey | Chicago | Anderson-Manson (3.8) Maley-Manson (3) |
| Dec 21, 1988 Wed | | Washington | Chicago | Hunter-Bassen (2) Stevens-Thomas (6.5) |
| Dec 23, 1988 Fri | | Detroit | Chicago | (Rough) Nill-Bassen (3) (Almost) King-McGill (2) Graves-Sutter (3) Halward-Vincelette (3) Probert-Manson (5.1) Kocur-Sutter (2.7) Scrum at 33:03 (3) King-McGill (7.5) Kocur-Vaive (2) Frycer-Yawney (1) Norwood-Eagles (2) Probert-McGill (3) Line Brawl at 59:44 Nill-Vincelette (6) Higgins-Graham Pavese-Manson (3.3) |
| Dec 26, 1988 Mon | | St. Louis | Chicago | Raglan-Murray (3) |
| Dec 28, 1988 Wed | | Minnesota | Chicago | McRae-Sutter (7) (Rough) Ciccarelli-Savard Mini-Brawl at 60:00 |
| Dec 31, 1988 Sat | | Chicago | NY Rangers | Mini-Brawl at 39:09 Sutter-Hardy (3) Sanipass-Kennedy (2) |
| Jan 1, 1989 Sun | | Toronto | Chicago | Richardson-Sutter Leeman-Yawney |
| Jan 7, 1989 Sat | | Chicago | Washington | (Hit) Konroyd-Courtnall (6.3) Bassen-Hunter (3) Konroyd-Druce (7.5) Mackey-Hatcher (5) |
| Jan 8, 1989 Sun | | NY Islanders | Chicago | (Rough) LaFontaine-Manson (1) |
| Jan 11, 1989 Wed | | Detroit | Chicago | Kocur-McGill (6) |
| Jan 12, 1989 Thu | | Chicago | Buffalo | Add Fight |
| Jan 14, 1989 Sat | | Chicago | NY Islanders | Add Fight |
| Jan 16, 1989 Mon | | Edmonton | Chicago | Buchberger-Sanipass |
| Jan 18, 1989 Wed | | NY Rangers | Chicago | DeBlois-Eagles (3) Kennedy-Sanipass (6) |
| Jan 20, 1989 Fri | | Chicago | Detroit | Mackey-Graves (4) Graham-Kocur (2.5) |
| Jan 21, 1989 Sat | | Chicago | St. Louis | Creighton-Ewen Sutter-Cavallini |
| Jan 24, 1989 Tue | | Chicago | Vancouver | Mackey-Butcher (5) Vincelette-Melnyk (2) |
| Jan 25, 1989 Wed | | Chicago | Edmonton | Mackey-McClelland Wilson-Simpson |
| Jan 28, 1989 Sat | | Chicago | Calgary | Add Fight |
| Jan 30, 1989 Mon | | Toronto | Chicago | Add Fight |
| Feb 1, 1989 Wed | | Winnipeg | Chicago | Boschman-Yawney Brawl at 6:54 Taglianetti-Sutter Taglianetti-Sanipass Berry-Vincelette (Cheap) Berthiaume-Presley (2) |
| Feb 4, 1989 Sat | | Chicago | Toronto | Add Fight |
| Feb 5, 1989 Sun | | St. Louis | Chicago | Raglan-Mackey |
| Feb 10, 1989 Fri | | NY Islanders | Chicago | Pilon-Rychel (6) Pilon-Sutter (1) Nylund-Creighton (3) Diduck-Sanipass (6) (Cheap) unknown-Creighton |
| Feb 12, 1989 Sun | | Los Angeles | Chicago | Miller-Sanipass (5) Miller-Rychel (5) Baumgartner-Rychel (3) |
| Feb 14, 1989 Tue | | Chicago | Minnesota | Konroyd-DePalma (6) |
| Feb 15, 1989 Wed | | Washington | Chicago | Thomson-Sanipass |
| Feb 17, 1989 Fri | | Chicago | Detroit | Creighton-Norwood (4.5) McGill-Kocur (4) Yawney-Burr (5) Vincelette-Norwood (3) |
| Feb 19, 1989 Sun | | Montreal | Chicago | Martinson-Creighton Corson-Vincelette |
| Feb 22, 1989 Wed | | Minnesota | Chicago | Add Fight |
| Feb 25, 1989 Sat | | Chicago | Detroit | (Cheap) McGill-Burr (3) Manson-Kocur (7.8) (Rough) Belfour-Probert (3.5) McGill-Probert (3) |
| Feb 26, 1989 Sun | | Detroit | Chicago | (Hit) Probert-Graham Higgins-Sutter Houda-Creighton (3) |
| Mar 1, 1989 Wed | | Minnesota | Chicago | McRae-Manson (6.3) Babe-Yawney (3) Mini-Brawl at 49:29 MacLellan-Mackey (5) |
| Mar 4, 1989 Sat | | Chicago | Toronto | (Rough) Yawney-Marois (Hit) Wilson-Gill (6) Graham-Gill (5) |
| Mar 5, 1989 Sun | | St. Louis | Chicago | Add Fight |
| Mar 8, 1989 Wed | | New Jersey | Chicago | (Rough) Daneyko-Manson (Rough) Velischek-Noonan Daneyko-Manson (2) Brawl at 40:00 (5) |
| Mar 11, 1989 Sat | | Chicago | Philadelphia | Creighton-Kerr McGill-Secord (4) Yawney-Mellanby (5.3) Stapleton-Propp (4) |
| Mar 12, 1989 Sun | | Pittsburgh | Chicago | Loney-Sanipass (3) Dineen-Vincelette (5) |
| Mar 14, 1989 Tue | | Chicago | St. Louis | Add Fight |
| Mar 16, 1989 Thu | | Chicago | Minnesota | Sanipass-Tinordi Vincelette-Churla (Cheap) Murray-unknown Scrum at 40:00 Scrum at 48:11 Manson-Churla (2) Manson-Tinordi (Rough) Larmer-McRae unknown-Churla |
| Mar 18, 1989 Sat | | Chicago | New Jersey | Van Dorp-Maley (2) |
| Mar 19, 1989 Sun | | Detroit | Chicago | Robertson-Sutter King-McGill (8.3) (Rough) Robertson-Roenick Kocur-Van Dorp (7.4) (Rough) Nill-Van Dorp (Cheap) O'Connell-Bassen (6) Scrum at 38:11 (7) Robertson-Manson (4) (Cheap) MacLean-Creighton (5) Robertson-Creighton (2) |
| Mar 22, 1989 Wed | | Philadelphia | Chicago | Mellanby-Sutter (3) |
| Mar 25, 1989 Sat | | Chicago | Boston | Add Fight |
| Mar 26, 1989 Sun | | Calgary | Chicago | Glynn-Sutter Peplinski-Presley |
| Mar 29, 1989 Wed | | Quebec | Chicago | Stienburg-Van Dorp Moller-Presley |
| Apr 1, 1989 Sat | | Chicago | Hartford | Van Dorp-Jennings (2) |
| Apr 2, 1989 Sun | | Toronto | Chicago | Add Fight |
| Apr 5, 1989 Wed | Round 1 | Game 1 | Chicago | Detroit | Add Fight |
| Apr 6, 1989 Thu | Round 1 | Game 2 | Chicago | Detroit | (Hit) Chevrier-King (Rough) Manson-Gallant |
| Apr 8, 1989 Sat | Round 1 | Game 3 | Detroit | Chicago | (Almost) Norwood-Sutter (1) (Cheap) Gallant-Manson (Cheap) Gallant-Manson Robertson-Creighton (5) |
| Apr 9, 1989 Sun | Round 1 | Game 4 | Detroit | Chicago | (Hit) Delorme-Gilbert (2) Burr-Bassen (Cheap) Norwood-Bassen |
| Apr 11, 1989 Tue | Round 1 | Game 5 | Chicago | Detroit | (Rough) Brown-Gallant (2) (Rough) Thomas-Kocur (4) Scrum at 19:30 |
| Apr 13, 1989 Thu | Round 1 | Game 6 | Detroit | Chicago | Add Fight |
| Apr 18, 1989 Tue | QF | Game 1 | Chicago | St. Louis | Add Fight |
| Apr 20, 1989 Thu | QF | Game 2 | Chicago | St. Louis | Van Dorp-Ewen (6.7) |
| Apr 22, 1989 Sat | QF | Game 3 | St. Louis | Chicago | (Rough) Lowry-Sutter (Rough) Featherstone-Presley (Rough) Benning-Gilbert Cavallini-McGill (1) (Rough) Featherstone-Manson |
| Apr 24, 1989 Mon | QF | Game 4 | St. Louis | Chicago | (Rough) Evans-Manson (Rough) Tilley-Gilbert (Rough) Lalor-Murray (Rough) Evans-Bassen |
| Apr 26, 1989 Wed | QF | Game 5 | Chicago | St. Louis | Add Fight |
| May 2, 1989 Tue | SF | Game 1 | Chicago | Calgary | Scrum (3) (Rough) Brown-Roberts Abuse at 18:38 (2) |
| May 4, 1989 Thu | SF | Game 2 | Chicago | Calgary | Add Fight |
| May 6, 1989 Sat | SF | Game 3 | Calgary | Chicago | (Hit) Gilmour-Manson (4) (Cheap) MacInnis-Presley (3) (Cheap) Mullen-Murray (3) (Rough) Otto-Van Dorp (Rough) Ramage-Graham (Cheap) Loob-Brown (4) Mini-Brawl at 34:14 (Rough) Nattress-Gilbert Brawl at 60:00 (9) McCrimmon-Larmer (4) Peplinski-Manson (4) |
| May 8, 1989 Mon | SF | Game 4 | Calgary | Chicago | (Rough) Otto-Bassen Scrum at 35:17 (2) (Rough) Roberts-Murray |
| May 10, 1989 Wed | SF | Game 5 | Chicago | Calgary | Sutter-MacLellan (5) |