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| Date / Time | Away / Home Team | Away / Home Player |
| Dec 21, 1999 | Pittsburgh Penguins | Steve Leach |
| 3pd 17:48 | New York Islanders | Dave Scatchard |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 20, 1999 | Toronto Maple Leafs | Tie Domi |
| 1pd 12:30 | Florida Panthers | Paul Laus |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 19, 1999 | Tampa Bay Lightning | Reid Simpson |
| 1pd 07:45 | New York Rangers | Stephane Quintal |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 18, 1999 | Chicago Blackhawks | Bryan McCabe |
| 3pd 16:09 | Los Angeles Kings | Ian Laperriere |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 18, 1999 | Chicago Blackhawks | Ryan VandenBussche |
| 1pd 13:12 | Los Angeles Kings | Sean O'Donnell |
| Other Penalties: VandenBussche received a misconduct. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 18, 1999 | Boston Bruins | Joe Murphy |
| 3pd 03:05 | St. Louis Blues | Tyson Nash |
| Other Penalties: Murphy received a game misconduct. Tyson Nash did not receive a fighting major. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 17, 1999 | Chicago Blackhawks | Brad Brown |
| 3pd 07:31 | Anaheim Ducks | Jim McKenzie |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 17, 1999 | Dallas Stars | Jamie Langenbrunner |
| 3pd 00:27 | Edmonton Oilers | Tom Poti |
| Other Penalties: Langenbrunner received a roughing. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 17, 1999 | Washington Capitals | Mike Eagles |
| 3pd 07:28 | New York Rangers | Todd Harvey |
| Other Penalties: Both players received roughings. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 17, 1999 | Boston Bruins | Rob DiMaio |
| 1pd 03:42 | Atlanta Thrashers | Denny Lambert |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 17, 1999 | Boston Bruins | Joe Murphy |
| 1pd 00:09 | Atlanta Thrashers | Johan Garpenlov |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 15, 1999 | Anaheim Ducks | Stu Grimson |
| 2pd 04:40 | Colorado Avalanche | Jeff Odgers |
| Other Penalties: Grimson received a charging. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 15, 1999 | Anaheim Ducks | Jim McKenzie |
| 1pd 02:35 | Colorado Avalanche | Sami Helenius |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 15, 1999 | New York Islanders | Eric Cairns |
| 3pd 16:50 | Toronto Maple Leafs | Tie Domi |
| Date / Time | Away / Home Team | Away / Home Player |
| Dec 15, 1999 | Edmonton Oilers | Sean Brown |
| 2pd 19:59 | Detroit Red Wings | Martin Lapointe |