| Sep 20, 1985 Fri | Preseason | Montreal | Edmonton | Kordic-McClelland (8.7) McPhee-Smith Lalor-McClelland Turcotte-Graves Corson-Krushelnyski |
| Sep 22, 1985 Sun | Preseason | Montreal | Winnipeg | Skrudland-Silk Rooney-Nill |
| Sep 26, 1985 Thu | Preseason | Edmonton | Montreal | Beukeboom-Corson |
| Sep 29, 1985 Sun | Preseason | Montreal | Quebec | McPhee-Mann Momesso-Julien Turcotte-Gillis |
| Sep 30, 1985 Mon | Preseason | Pittsburgh | Montreal | Buskas-Nilan Bodger-Nilan |
| Oct 1, 1985 Tue | Preseason | Pittsburgh | Montreal | Cunneyworth-Kordic Nolan-Corson |
| Oct 4, 1985 Fri | Preseason | Boston | Montreal | Blum-Rooney Byers-Campedelli Blum-McPhee |
| Oct 5, 1985 Sat | Preseason | Boston | Montreal | Add Fight |
| Oct 6, 1985 Sun | Preseason | Quebec | Montreal | Eagles-Chelios Price-Smith Gillis-Richer |
| Oct 10, 1985 Thu | | Montreal | Pittsburgh | Add Fight |
| Oct 12, 1985 Sat | | Chicago | Montreal | Collision at 30:00 (4) Secord-Nilan (4) |
| Oct 13, 1985 Sun | | Montreal | Boston | Nilan-Markwart (6) (Cheap) Nilan-Middleton McPhee-Kluzak Rooney-Crowder |
| Oct 16, 1985 Wed | | Buffalo | Montreal | Add Fight |
| Oct 19, 1985 Sat | | Montreal | Hartford | Add Fight |
| Oct 21, 1985 Mon | | Quebec | Montreal | (Cheap) Stastny-Richer (Rough) Ashton-Chelios Finn-Momesso (5) (Rough) Finn-Momesso (Rough) Marois-Smith Gillis-Lalor (3.5) |
| Oct 23, 1985 Wed | | Montreal | Buffalo | (Cheap) Svoboda-Tucker Rooney-Playfair (5) |
| Oct 26, 1985 Sat | | Hartford | Montreal | Gavin-Rooney (4) Robertson-Smith (3) MacDermid-McPhee (1) (Hit) MacDermid-Svoboda Robertson-Rooney (3.5) |
| Oct 29, 1985 Tue | | Montreal | Quebec | Lalor-Paiement (3) Carbonneau-Hunter (2) (Rough) Smith-Gillis (Rough) Smith-Gillis McPhee-Babych (3) |
| Oct 30, 1985 Wed | | Philadelphia | Montreal | (Rough) Tocchet-Carbonneau (Rough) Sutter-Lalor (Rough) Tocchet-Ludwig |
| Nov 2, 1985 Sat | | Pittsburgh | Montreal | Frawley-Momesso (4) |
| Nov 5, 1985 Tue | | Montreal | Hartford | Momesso-Paterson (2) Nilan-Robertson |
| Nov 6, 1985 Wed | | Montreal | Minnesota | Lemieux-Richter |
| Nov 9, 1985 Sat | | Montreal | Los Angeles | Nilan-Tuer (3) |
| Nov 12, 1985 Tue | | Montreal | NY Islanders | Add Fight |
| Nov 13, 1985 Wed | | Montreal | NY Rangers | (Rough) Lemieux-Brooke Nilan-Ridley (3) Richer-Richmond (1) Nilan-Patrick (6) |
| Nov 16, 1985 Sat | | NY Rangers | Montreal | Richmond-Tremblay (3) (Rough) Osborne-Chelios |
| Nov 18, 1985 Mon | | Boston | Montreal | Curran-Nilan (5) Courtnall-Chelios (3) Kluzak-Momesso (5) Crowder-McPhee Curran-Nilan (6.5) |
| Nov 20, 1985 Wed | | Edmonton | Montreal | Add Fight |
| Nov 23, 1985 Sat | | Calgary | Montreal | Add Fight |
| Nov 27, 1985 Wed | | Montreal | Washington | Add Fight |
| Nov 29, 1985 Fri | | Montreal | Buffalo | Walter-Ruff (2) Nilan-Dykstra (6.5) Lalor-Ruff (3) |
| Nov 30, 1985 Sat | | Detroit | Montreal | Kocur-McPhee (2.8) Kocur-Walter (3.7) |
| Dec 2, 1985 Mon | | Vancouver | Montreal | Add Fight |
| Dec 5, 1985 Thu | | Montreal | Boston | (Hit) Momesso-Thelven Nilan-Miller (7.4) Kurvers-Markwart (5) Scrum at 19:47 Nilan-Miller (6.7) Line Brawl at 33:34 (3) Chelios-Curran (4) Lalor-Markwart (2.5) |
| Dec 7, 1985 Sat | | Montreal | Toronto | Add Fight |
| Dec 11, 1985 Wed | | Montreal | Hartford | Kordic-Robertson (6) |
| Dec 12, 1985 Thu | | Montreal | Philadelphia | Add Fight |
| Dec 14, 1985 Sat | | Chicago | Montreal | Dupont-Kordic (5.7) |
| Dec 16, 1985 Mon | | Hartford | Montreal | Murzyn-Tremblay (3) Robertson-McPhee Samuelsson-DeBlois (4) Murzyn-Nilan (6) Robertson-Nilan (3.7) |
| Dec 18, 1985 Wed | | Quebec | Montreal | Add Fight |
| Dec 19, 1985 Thu | | Montreal | Quebec | Add Fight |
| Dec 21, 1985 Sat | | Buffalo | Montreal | Add Fight |
| Dec 27, 1985 Fri | | Montreal | New Jersey | Add Fight |
| Dec 28, 1985 Sat | | New Jersey | Montreal | (Hit) Hiemer-Ludwig Hiemer-Nilan Verbeek-Carbonneau Lorimer-Smith Muller-Rooney |
| Jan 1, 1986 Wed | | Montreal | Toronto | McPhee-Smith (5) |
| Jan 3, 1986 Fri | | Montreal | Winnipeg | Add Fight |
| Jan 4, 1986 Sat | | Montreal | Calgary | (Hit) Robinson-Hunter (Hit) Walter-Bourgeois (Cheap) Lemieux-McDonald Nilan-Hunter (3) Walter-Bourgeois (2) |
| Jan 6, 1986 Mon | | St. Louis | Montreal | Add Fight |
| Jan 8, 1986 Wed | | Boston | Montreal | (Hit) Nienhuis-Walter Markwart-Rooney (6.5) Blum-McPhee (5) Miller-Nilan (8.2) |
| Jan 10, 1986 Fri | | Montreal | NY Rangers | Smith-Greschner (3) Nilan-Osborne Ludwig-Ridley |
| Jan 11, 1986 Sat | | Edmonton | Montreal | (Cheap) Jackson-Carbonneau Jackson-Nilan (6) |
| Jan 15, 1986 Wed | | Winnipeg | Montreal | Boschman-Skrudland |
| Jan 17, 1986 Fri | | Montreal | Buffalo | Add Fight |
| Jan 18, 1986 Sat | | NY Islanders | Montreal | Add Fight |
| Jan 20, 1986 Mon | | Montreal | Quebec | Nilan-Paiement |
| Jan 22, 1986 Wed | | Montreal | Chicago | (Rough) Ludwig-Secord |
| Jan 23, 1986 Thu | | Montreal | Minnesota | Add Fight |
| Jan 25, 1986 Sat | | Toronto | Montreal | Add Fight |
| Jan 27, 1986 Mon | | Buffalo | Montreal | Add Fight |
| Jan 29, 1986 Wed | | Quebec | Montreal | (Rough) Gillis-Kurvers (Cheap) unknown-Robinson Kumpel-DeBlois (Rough) Hunter-Walter (Rough) Stastny-Carbonneau (Rough) Gillis-Robinson |
| Feb 1, 1986 Sat | | Boston | Montreal | Add Fight |
| Feb 5, 1986 Wed | | Montreal | Quebec | Nilan-Donnelly (6.3) Nilan-Donnelly (4.3) Rooney-Shaw Nilan-Eagles |
| Feb 7, 1986 Fri | | Montreal | Washington | (Hit) Nilan-Stevens |
| Feb 8, 1986 Sat | | Montreal | Detroit | Nilan-Probert (2.8) Rooney-Young Svoboda-Gare |
| Feb 10, 1986 Mon | | Minnesota | Montreal | (Rough) Casey-Robinson |
| Feb 13, 1986 Thu | | Montreal | New Jersey | Add Fight |
| Feb 15, 1986 Sat | | Philadelphia | Montreal | Tocchet-Kurvers (3) (Rough) McCrimmon-Richer |
| Feb 17, 1986 Mon | | Los Angeles | Montreal | Add Fight |
| Feb 19, 1986 Wed | | Washington | Montreal | Add Fight |
| Feb 22, 1986 Sat | | Hartford | Montreal | Samuelsson-Nilan (6) |
| Feb 24, 1986 Mon | | Montreal | Edmonton | Nilan-McSorley (1) |
| Feb 26, 1986 Wed | | Montreal | Vancouver | Add Fight |
| Mar 1, 1986 Sat | | Montreal | Los Angeles | Nilan-Wells (5) |
| Mar 4, 1986 Tue | | Montreal | NY Islanders | McPhee-Sutter |
| Mar 6, 1986 Thu | | St. Louis | Montreal | Add Fight |
| Mar 8, 1986 Sat | | Boston | Montreal | (Rough) Linseman-Nilan (Rough) Miller-Rooney Markwart-Rooney (2) (Almost) Miller-Rooney (Almost) Keans-Richer Miller-Rooney (3) (Rough) Crowder-Ludwig |
| Mar 10, 1986 Mon | | Hartford | Montreal | Add Fight |
| Mar 12, 1986 Wed | | Vancouver | Montreal | Coxe-Rooney (6.8) Lanthier-Nilan |
| Mar 13, 1986 Thu | | Montreal | Boston | Lalor-Pasin |
| Mar 15, 1986 Sat | | Calgary | Montreal | Add Fight |
| Mar 17, 1986 Mon | | Quebec | Montreal | Picard-Nilan (Rough) Gillis-Ludwig Ashton-Nilan (4) |
| Mar 19, 1986 Wed | | Montreal | Winnipeg | Add Fight |
| Mar 22, 1986 Sat | | Montreal | St. Louis | Rooney-Pavese (Rough) McPhee-Ramage McPhee-Norwood (Rough) Carbonneau-Federko |
| Mar 26, 1986 Wed | | Montreal | Hartford | (Rough) McPhee-Robertson (Almost) Skrudland-Murzyn Rooney-Babych (6) (Rough) Chelios-Turgeon Chelios-Turgeon |
| Mar 27, 1986 Thu | | Montreal | Boston | Nilan-Miller (7) |
| Mar 29, 1986 Sat | | Pittsburgh | Montreal | (Rough) Hannan-Chelios Loney-Nilan (6) Hannan-Chelios |
| Apr 2, 1986 Wed | | Detroit | Montreal | Event |
| Apr 4, 1986 Fri | | Montreal | Buffalo | Nilan-Foligno Lemieux-Hajt |
| Apr 5, 1986 Sat | | Buffalo | Montreal | (Almost) Smith-Richer Smith-Richer |
| Apr 9, 1986 Wed | Round 1 | Game 1 | Boston | Montreal | Simmer-McPhee (Refused) Miller-Kordic (Rough) Pederson-Skrudland Mini-Brawl at 25:57 Sleigher-Robinson (4) (Hit) Kluzak-Lemieux (Hit) Sleigher-Roy (5) Sleigher-Robinson (6) Line Brawl at 57:59 (8) Linseman-Nilan (3) Crowder-McPhee (8) Milbury-Richer (5) Linseman-Svoboda (Rough) Burridge-Chelios (Cheap) Curran-unknown Curran-Chelios |
| Apr 10, 1986 Thu | Round 1 | Game 2 | Boston | Montreal | (Rough) Kluzak-Nilan Miller-Kordic (8.1) |
| Apr 12, 1986 Sat | Round 1 | Game 3 | Montreal | Boston | (Rough) Skrudland-Nienhuis (Cheap) Lemieux-Courtnall |
| Apr 17, 1986 Thu | QF | Game 1 | Hartford | Montreal | Robertson-Kordic (6.5) (Rough) Robertson-Lemieux |
| Apr 19, 1986 Sat | QF | Game 2 | Hartford | Montreal | (Rough) Gavin-Skrudland (Rough) Samuelsson-Skrudland Robertson-Kordic (6) |
| Apr 21, 1986 Mon | QF | Game 3 | Montreal | Hartford | DeBlois-Robertson |
| Apr 23, 1986 Wed | QF | Game 4 | Montreal | Hartford | (Rough) Chelios-MacDermid Scrum at 30:04 (Rough) Lemieux-Dineen |
| Apr 25, 1986 Fri | QF | Game 5 | Hartford | Montreal | (Rough) Robertson-Nilan Robertson-Nilan (3) (Rough) Francis-Skrudland Dineen-Smith Scrum at 55:00 (2) |
| Apr 27, 1986 Sun | QF | Game 6 | Montreal | Hartford | (Rough) Carbonneau-Dineen (2) (Rough) McPhee-Quenneville Nilan-Robertson (4) Scrum at 36:10 (3) (Rough) Skrudland-Bothwell (Rough) Richer-Dineen Scrum at 57:00 (3) (Cheap) Lemieux-Samuelsson |
| Apr 29, 1986 Tue | QF | Game 7 | Hartford | Montreal | Injury at 59:12 (Rough) Kleinendorst-Nilan |
| May 1, 1986 Thu | SF | Game 1 | NY Rangers | Montreal | (Rough) Allison-McPhee |
| May 3, 1986 Sat | SF | Game 2 | NY Rangers | Montreal | (Hit) Laidlaw-Gingras (Cheap) McPhee-Carbonneau McPhee-Kordic (8) Paiement-Nilan (2) (Rough) Allison-Richer (Rough) Osborne-Robinson |
| May 5, 1986 Mon | SF | Game 3 | Montreal | NY Rangers | (Rough) Green-Allison (2) (Rough) Lalor-Allison |
| May 7, 1986 Wed | SF | Game 4 | Montreal | NY Rangers | (Almost) Ludwig-Crawford Scrum (Rough) Lemieux-Patrick (Rough) Ludwig-Ridley Nilan-Melnyk (6.8) (Cheap) Chelios-Sandstrom Lemieux-Patrick (6.5) |
| May 9, 1986 Fri | SF | Game 5 | NY Rangers | Montreal | Add Fight |
| May 16, 1986 Fri | Final | Game 1 | Montreal | Calgary | Nilan-Hunter Scrum at 40:00 |
| May 18, 1986 Sun | Final | Game 2 | Montreal | Calgary | (Rough) Gainey-Peplinski Nilan-Hunter (4.8) |
| May 20, 1986 Tue | Final | Game 3 | Calgary | Montreal | (Hit) Mullen-Gingras (Rough) Quinn-Skrudland Mini-Brawl at 19:39 Sheehy-Nilan (4) Hunter-Kordic (8.2) (Rough) MacInnis-Walter Mini-Brawl at 38:32 Hunter-Nilan (3) |
| May 22, 1986 Thu | Final | Game 4 | Calgary | Montreal | Scrum at 1:31 Sheehy-Smith (3) Bench-Clearing Brawl at 60:00 (5) Baxter-Chelios Peplinski-Lemieux (4.7) Bozek-Carbonneau Tonelli-Lalor |
| May 24, 1986 Sat | Final | Game 5 | Montreal | Calgary | (Hit) Walter-Baxter (Hit) Carbonneau-Baxter |