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| Date | Time | Player | Team | Opponent |
| Oct 02, 1999 | 2pd 16:32 | Patrick Poulin | TOR | Bryan Berard |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Oct 02, 1999 | 3pd 20:00 | Turner Stevenson | TOR | Chris McAllister |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Oct 08, 1999 | 1pd 05:41 | Scott Thornton | @CAL | Wade Belak |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Oct 08, 1999 | 1pd 08:30 | Craig Rivet | @CAL | Derek Morris |
| Comments: Other Penalties: Jim Cummins received a spearing major and game misconduct; Marc Savard a slashing minor. | ||||
| Date | Time | Player | Team | Opponent |
| Oct 08, 1999 | 1pd 17:30 | Turner Stevenson | @CAL | Wade Belak |
| Comments: Other Penalties: Stevenson received a roughing minor; Belak an instigator and misconduct. | ||||
| Date | Time | Player | Team | Opponent |
| Oct 20, 1999 | 2pd 10:59 | Jim Cummins | COL | Jeff Odgers |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Oct 23, 1999 | 1pd 09:10 | Jim Cummins | @TOR | Tie Domi |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Oct 27, 1999 | 1pd 05:18 | Jim Cummins | CHI | Brad Brown |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Nov 13, 1999 | 3pd 10:29 | Shayne Corson | ATL | Kelly Buchberger |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Nov 16, 1999 | 1pd 01:02 | Shayne Corson | SAN | Owen Nolan |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Nov 18, 1999 | 1pd 04:16 | Jim Cummins | @NAS | Scott Walker |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Nov 18, 1999 | 1pd 09:56 | Arron Asham | @NAS | Drake Berehowsky |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Nov 18, 1999 | 1pd 10:38 | Brian Savage | @NAS | Rob Valicevic |
| Comments: Other Penalties: Savage received an instigator and misconduct. | ||||
| Date | Time | Player | Team | Opponent |
| Nov 27, 1999 | 1pd 00:32 | Jim Cummins | VAN | Donald Brashear |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Nov 27, 1999 | 1pd 00:50 | Arron Asham | VAN | Dave Scatchard |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Nov 27, 1999 | 1pd 15:24 | Shayne Corson | VAN | Ed Jovanovski |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Dec 01, 1999 | 1pd 07:30 | Arron Asham | DAL | Brad Lukowich |
| Comments: Asham and Lukowich drop them and grab a hold of one another. Lukowich comes up short with two punches. Asham responds with one, but Lukowich ducks it. Asham holds him at arms-length and lands two shots as Lukowich tries for one of his own, but misses. Asham pops Lukowich square in the nose again, this time causing some blood. Asham then lands another one. Lukowich seems frustrated that he's out of reach as Asham lands one more. They exchange punches that don't seem to connect, and with that they hold on until the linesman come in. | ||||
| Voted winner: Arron Asham (93.5%) - Voted rating: 6.3 | ||||
| Date | Time | Player | Team | Opponent |
| Dec 04, 1999 | 1pd 09:21 | Scott Thornton | PHI | Craig Berube |
| Comments: Other Penalties: Thornton an instigator and misconduct; Berube a goalie interference. | ||||
| Date | Time | Player | Team | Opponent |
| Dec 11, 1999 | 1pd 02:38 | Jim Cummins | LOS | Steve McKenna |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Dec 11, 1999 | 2pd 02:35 | Arron Asham | LOS | Ian Laperriere |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Jan 15, 2000 | 1pd 02:42 | Scott Thornton | BOS | Marty McSorley |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Jan 29, 2000 | 1pd 11:10 | Igor Ulanov | PHI | Luke Richardson |
| Comments: Other Penalties: Ulanov received an interference; Richardson an instigator, misconduct and game misconduct. | ||||
| Date | Time | Player | Team | Opponent |
| Feb 14, 2000 | 2pd 17:35 | Igor Ulanov | FLA | Peter Worrell |
| Comments: Other Players: Both Players received game misconducts. | ||||
| Date | Time | Player | Team | Opponent |
| Feb 14, 2000 | 2pd 17:47 | Eric Weinrich | FLA | Scott Mellanby |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Feb 16, 2000 | 1pd 02:16 | Dave Morissette | @ATL | Matt Johnson |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Mar 04, 2000 | 3pd 02:34 | Shayne Corson | @TOR | Tie Domi |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Mar 06, 2000 | 1pd 19:28 | Craig Rivet | ATL | Geordie Kinnear |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Mar 06, 2000 | 2pd 20:00 | Turner Stevenson | ATL | Denny Lambert |
| Comments: Other Penalties: Rumun Ndur received a double roughing a misconduct; Sheldon Souray a roughing and misconduct. | ||||
| Date | Time | Player | Team | Opponent |
| Mar 11, 2000 | 1pd 18:59 | Shayne Corson | BOS | Cameron Mann |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Mar 14, 2000 | 1pd 14:34 | Benoit Brunet | TAM | Petr Svoboda |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Mar 18, 2000 | 2pd 03:56 | Dainius Zubrus | CAR | Tommy Westlund |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Mar 20, 2000 | 1pd 02:27 | Jim Cummins | @BUF | Rob Ray |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Mar 25, 2000 | 1pd 03:25 | Sheldon Souray | @FLA | Paul Laus |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Apr 06, 2000 | 3pd 01:53 | Sheldon Souray | TAM | Gordie Dwyer |
| Comments: | ||||
| Date | Time | Player | Team | Opponent |
| Apr 06, 2000 | 3pd 15:25 | Dainius Zubrus | TAM | Ben Clymer |
| Comments: Other Penalties: Both players received cross checkings. | ||||
If the opponent's team is preceded by a @ symbol, then opponent's team was the home team. Otherwise the Montreal Canadiens were the home team.