| 02 Oct 99 | r00   | Dallas StarsDallas Stars | 6 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 07 Oct 99 | r00 | New Jersey DevilsNew Jersey De | 5 - 7 | Pittsburgh PenguinsPittsburgh Pe |
| 08 Oct 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 3 | Colorado AvalancheColorado Aval |
| 14 Oct 99 | r00 | New York RangersNew York Rang | 2 - 5 | Pittsburgh PenguinsPittsburgh Pe |
| 16 Oct 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 3 | Chicago BlackhawksChicago Black |
| 23 Oct 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 2 - 3 | Carolina HurricanesCarolina Hurr |
| 28 Oct 99 | r00 | Anaheim DucksAnaheim Ducks | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 29 Oct 99 | r00 | Los Angeles KingsLos Angeles K | 5 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 31 Oct 99 | r00 | San Jose SharksSan Jose Shar | 1 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 03 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 5 | Los Angeles KingsLos Angeles K |
| 05 Nov 99 | r00 | Ottawa SenatorsOttawa Senato | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 07 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 7 | Tampa Bay LightningTampa Bay Lig |
| 11 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 5 - 4 | Montreal CanadiensMontreal Cana |
| 13 Nov 99 | r00 | Detroit Red WingsDetroit Red W | 3 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 14 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 6 - 2 | Nashville PredatorsNashville Pre |
| 17 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | Buffalo SabresBuffalo Sabre |
| 19 Nov 99 | r00 | Tampa Bay LightningTampa Bay Lig | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 21 Nov 99 | r00 | Florida PanthersFlorida Panth | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 24 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 1 | Toronto Maple LeafsToronto Maple |
| 27 Nov 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 5 - 0 | Ottawa SenatorsOttawa Senato |
| 28 Nov 99 | r00 | Carolina HurricanesCarolina Hurr | 5 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 01 Dec 99 | r00 | Buffalo SabresBuffalo Sabre | 1 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 03 Dec 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 2 - 5 | San Jose SharksSan Jose Shar |
| 05 Dec 99 | r00 | Toronto Maple LeafsToronto Maple | 3 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 08 Dec 99 | r00 | New Jersey DevilsNew Jersey De | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 10 Dec 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 0 | Washington CapitalsWashington Ca |
| 12 Dec 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 2 | Arizona CoyotesArizona Coyot |
| 15 Dec 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 2 | Boston BruinsBoston Bruins |
| 16 Dec 99 | r00 | Carolina HurricanesCarolina Hurr | 3 - 6 | Pittsburgh PenguinsPittsburgh Pe |
| 19 Dec 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 2 - 5 | Florida PanthersFlorida Panth |
| 21 Dec 99 | r00 | Montreal CanadiensMontreal Cana | 5 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 22 Dec 99 | r00 | New York IslandersNew York Isla | 0 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 24 Dec 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 3 | Tampa Bay LightningTampa Bay Lig |
| 27 Dec 99 | r00 | Chicago BlackhawksChicago Black | 2 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 30 Dec 99 | r00 | Washington CapitalsWashington Ca | 3 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 31 Dec 99 | r00 | Pittsburgh PenguinsPittsburgh Pe | 9 - 3 | New York IslandersNew York Isla |
| 03 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 3 | Detroit Red WingsDetroit Red W |
| 06 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 1 - 3 | New Jersey DevilsNew Jersey De |
| 08 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 5 - 2 | Toronto Maple LeafsToronto Maple |
| 09 Jan 00 | r00 | Philadelphia FlyersPhiladelphia | 6 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 13 Jan 00 | r00 | Arizona CoyotesArizona Coyot | 3 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 14 Jan 00 | r00 | Colorado AvalancheColorado Aval | 4 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 16 Jan 00 | r00 | Nashville PredatorsNashville Pre | 4 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 20 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 1 | St. Louis BluesSt. Louis Blu |
| 23 Jan 00 | r00 | Montreal CanadiensMontreal Cana | 4 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 24 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 4 | Philadelphia FlyersPhiladelphia |
| 26 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 4 | New York RangersNew York Rang |
| 28 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 1 | Atlanta ThrashersAtlanta Thras |
| 30 Jan 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 1 - 7 | Anaheim DucksAnaheim Ducks |
| 01 Feb 00 | r00 | Atlanta ThrashersAtlanta Thras | 1 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 02 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | Washington CapitalsWashington Ca |
| 04 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 2 | New York IslandersNew York Isla |
| 10 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 5 - 2 | Atlanta ThrashersAtlanta Thras |
| 12 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 2 - 2 | Edmonton OilersEdmonton Oile |
| 13 Feb 00 | r00 | New York IslandersNew York Isla | 5 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 15 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 0 | Vancouver CanucksVancouver Can |
| 17 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 1 - 1 | Buffalo SabresBuffalo Sabre |
| 20 Feb 00 | r00 | Florida PanthersFlorida Panth | 1 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 22 Feb 00 | r00 | Tampa Bay LightningTampa Bay Lig | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 23 Feb 00 | r00 | New York RangersNew York Rang | 4 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 25 Feb 00 | r00 | Philadelphia FlyersPhiladelphia | 4 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 27 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 2 - 2 | Boston BruinsBoston Bruins |
| 29 Feb 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 1 - 1 | Ottawa SenatorsOttawa Senato |
| 02 Mar 00 | r00 | Calgary FlamesCalgary Flame | 8 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 05 Mar 00 | r00 | Edmonton OilersEdmonton Oile | 2 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 09 Mar 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 0 - 3 | Montreal CanadiensMontreal Cana |
| 10 Mar 00 | r00 | Ottawa SenatorsOttawa Senato | 7 - 0 | Pittsburgh PenguinsPittsburgh Pe |
| 12 Mar 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 1 | New York RangersNew York Rang |
| 14 Mar 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 2 - 3 | New Jersey DevilsNew Jersey De |
| 17 Mar 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 4 - 2 | Florida PanthersFlorida Panth |
| 19 Mar 00 | r00 | Boston BruinsBoston Bruins | 3 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 20 Mar 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 5 - 4 | New York RangersNew York Rang |
| 22 Mar 00 | r00 | New York IslandersNew York Isla | 2 - 8 | Pittsburgh PenguinsPittsburgh Pe |
| 25 Mar 00 | r00 | Atlanta ThrashersAtlanta Thras | 3 - 5 | Pittsburgh PenguinsPittsburgh Pe |
| 27 Mar 00 | r00 | Philadelphia FlyersPhiladelphia | 3 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 29 Mar 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | New Jersey DevilsNew Jersey De |
| 31 Mar 00 | r00 | Washington CapitalsWashington Ca | 3 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 02 Apr 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 2 - 3 | Philadelphia FlyersPhiladelphia |
| 03 Apr 00 | r00 | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | Carolina HurricanesCarolina Hurr |
| 05 Apr 00 | r00 | Toronto Maple LeafsToronto Maple | 2 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 07 Apr 00 | r00 | Buffalo SabresBuffalo Sabre | 1 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 09 Apr 00 | r00 | Boston BruinsBoston Bruins | 3 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| |
| 13 Apr 00 | Playoff | Washington CapitalsWashington Ca | 0 - 7 | Pittsburgh PenguinsPittsburgh Pe |
| 15 Apr 00 | Playoff | Pittsburgh PenguinsPittsburgh Pe | 2 - 1 | Washington CapitalsWashington Ca |
| 17 Apr 00 | Playoff | Pittsburgh PenguinsPittsburgh Pe | 4 - 3 | Washington CapitalsWashington Ca |
| 19 Apr 00 | Playoff | Washington CapitalsWashington Ca | 3 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 21 Apr 00 | Playoff | Washington CapitalsWashington Ca | 1 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| |
| 27 Apr 00 | QF | Philadelphia FlyersPhiladelphia | 0 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 29 Apr 00 | QF | Philadelphia FlyersPhiladelphia | 1 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 02 May 00 | QF | Pittsburgh PenguinsPittsburgh Pe | 3 - 4 | Philadelphia FlyersPhiladelphia |
| 04 May 00 | QF | Pittsburgh PenguinsPittsburgh Pe | 1 - 2 | Philadelphia FlyersPhiladelphia |
| 07 May 00 | QF | Philadelphia FlyersPhiladelphia | 6 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 09 May 00 | QF | Pittsburgh PenguinsPittsburgh Pe | 1 - 2 | Philadelphia FlyersPhiladelphia |
Team 1999-2000 Schedules
Anaheim Ducks
Boston Bruins
Buffalo Sabres
Calgary Flames
Carolina Hurricanes
Chicago Blackhawks
Colorado Avalanche
Columbus Blue Jackets
Dallas Stars
Detroit Red Wings
Edmonton Oilers
Florida Panthers
Los Angeles Kings
Minnesota Wild
Montreal Canadiens
Nashville Predators
New Jersey Devils
New York Islanders
New York Rangers
Ottawa Senators
Philadelphia Flyers
Pittsburgh Penguins
San Jose Sharks
Seattle Kraken
St. Louis Blues
Tampa Bay Lightning
Toronto Maple Leafs
Utah Mammoth
Vancouver Canucks
Vegas Golden Knights
Washington Capitals
Winnipeg Jets
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