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| Date / Time | Away / Home Team | Away / Home Player |
| Oct 17, 1999 | Buffalo Sabres | Jean-Luc Grand-Pierre |
| 1pd 02:51 | Philadelphia Flyers | Sandy McCarthy |
| Other Penalties: Paul Kruse and Luke Richardson both received unsportsmanlike conduct penalties. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 17, 1999 | Atlanta Thrashers | Matt Johnson |
| 1pd 00:14 | New York Rangers | Darren Langdon |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 16, 1999 | Ottawa Senators | Andre Roy |
| 2pd 07:59 | Colorado Avalanche | Chris Dingman |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 16, 1999 | Ottawa Senators | Kevin Dineen |
| 1pd 06:48 | Colorado Avalanche | Adam Deadmarsh |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 16, 1999 | Dallas Stars | Jamie Pushor |
| 2pd 03:47 | Nashville Predators | Patrick Cote |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 16, 1999 | New York Islanders | Brad Isbister |
| 1pd 02:25 | New Jersey Devils | Sheldon Souray |
| Relatively even, Souray throwing more. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 16, 1999 | Anaheim Ducks | Jim McKenzie |
| 1pd 02:38 | Florida Panthers | Paul Laus |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 15, 1999 | Los Angeles Kings | Aki Berg |
| 3pd 14:20 | Calgary Flames | Rene Corbet |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 15, 1999 | Los Angeles Kings | Marko Tuomainen |
| 2pd 17:11 | Calgary Flames | Steve Smith |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 15, 1999 | Boston Bruins | Sean Pronger |
| 2pd 16:55 | Dallas Stars | Warren Luhning |
| Other Penalties: Luhning received a high sticking. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 14, 1999 | Pittsburgh Penguins | Matt Barnaby |
| 3pd 17:27 | New York Rangers | Todd Harvey |
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 13, 1999 | Calgary Flames | Wade Belak |
| 1pd 02:19 | Vancouver Canucks | Brad May |
| Other Penalties: May received a roughing minor. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 13, 1999 | Anaheim Ducks | Stu Grimson |
| 2pd 07:16 | New Jersey Devils | Krzysztof Oliwa |
| Other Penalties: Oliwa received a high sticking. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 12, 1999 | Philadelphia Flyers | Craig Berube |
| 2pd 02:38 | Washington Capitals | Brendan Witt |
| Other Penalties: Berube received a roughing minor. | ||
| Date / Time | Away / Home Team | Away / Home Player |
| Oct 11, 1999 | Carolina Hurricanes | Nolan Pratt |
| 1pd 15:30 | Calgary Flames | Bill Lindsay |