| 10 Oct 98 | r00        | New York IslandersNew York Isla | 3 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 14 Oct 98 | r00        | New Jersey DevilsNew Jersey De | 1 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 17 Oct 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 3 - 3 | New York RangersNew York Rang |
| 21 Oct 98 | r00        | Tampa Bay LightningTampa Bay Lig | 5 - 0 | Pittsburgh PenguinsPittsburgh Pe |
| 24 Oct 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 6 | Toronto Maple LeafsToronto Maple |
| 27 Oct 98 | r00        | Toronto Maple LeafsToronto Maple | 0 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 29 Oct 98 | r00        | Calgary FlamesCalgary Flame | 2 - 5 | Pittsburgh PenguinsPittsburgh Pe |
| 31 Oct 98 | r00        | Vancouver CanucksVancouver Can | 2 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 01 Nov 98 | r00        | Edmonton OilersEdmonton Oile | 4 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 04 Nov 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 4 | Philadelphia FlyersPhiladelphia |
| 06 Nov 98 | r00        | Ottawa SenatorsOttawa Senato | 2 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 08 Nov 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 0 - 0 | Boston BruinsBoston Bruins |
| 11 Nov 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | New York IslandersNew York Isla |
| 14 Nov 98 | r00        | New Jersey DevilsNew Jersey De | 4 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 15 Nov 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 0 | Florida PanthersFlorida Panth |
| 18 Nov 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 1 - 4 | Philadelphia FlyersPhiladelphia |
| 20 Nov 98 | r00        | Tampa Bay LightningTampa Bay Lig | 1 - 5 | Pittsburgh PenguinsPittsburgh Pe |
| 22 Nov 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 5 - 2 | Tampa Bay LightningTampa Bay Lig |
| 26 Nov 98 | r00        | Washington CapitalsWashington Ca | 5 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 28 Nov 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 2 | New York RangersNew York Rang |
| 29 Nov 98 | r00        | Montreal CanadiensMontreal Cana | 3 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 02 Dec 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 4 | Anaheim DucksAnaheim Ducks |
| 05 Dec 98 | r00        | Carolina HurricanesCarolina Hurr | 3 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 06 Dec 98 | r00        | Boston BruinsBoston Bruins | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 13 Dec 98 | r00        | St. Louis BluesSt. Louis Blu | 3 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 16 Dec 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | Tampa Bay LightningTampa Bay Lig |
| 17 Dec 98 | r00        | Florida PanthersFlorida Panth | 4 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 20 Dec 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 3 - 0 | Washington CapitalsWashington Ca |
| 22 Dec 98 | r00        | Toronto Maple LeafsToronto Maple | 7 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 23 Dec 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 0 - 3 | Los Angeles KingsLos Angeles K |
| 27 Dec 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 1 | Ottawa SenatorsOttawa Senato |
| 31 Dec 98 | r00        | Pittsburgh PenguinsPittsburgh Pe | 7 - 4 | Florida PanthersFlorida Panth |
| 03 Jan 99 | r00        | Florida PanthersFlorida Panth | 2 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 06 Jan 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 5 - 1 | Calgary FlamesCalgary Flame |
| 08 Jan 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 2 | Carolina HurricanesCarolina Hurr |
| 10 Jan 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 1 | St. Louis BluesSt. Louis Blu |
| 14 Jan 99 | r00        | Arizona CoyotesArizona Coyot | 5 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 16 Jan 99 | r00        | San Jose SharksSan Jose Shar | 3 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 17 Jan 99 | r00        | Los Angeles KingsLos Angeles K | 1 - 5 | Pittsburgh PenguinsPittsburgh Pe |
| 19 Jan 99 | r00        | Anaheim DucksAnaheim Ducks | 5 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 22 Jan 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 5 | New York IslandersNew York Isla |
| 27 Jan 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 3 - 5 | Carolina HurricanesCarolina Hurr |
| 29 Jan 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 6 - 0 | Toronto Maple LeafsToronto Maple |
| 31 Jan 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 5 - 2 | Boston BruinsBoston Bruins |
| 01 Feb 99 | r00        | Montreal CanadiensMontreal Cana | 3 - 5 | Pittsburgh PenguinsPittsburgh Pe |
| 03 Feb 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 5 - 3 | Buffalo SabresBuffalo Sabre |
| 06 Feb 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 3 - 0 | Florida PanthersFlorida Panth |
| 08 Feb 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 1 | Detroit Red WingsDetroit Red W |
| 10 Feb 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | Montreal CanadiensMontreal Cana |
| 12 Feb 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 6 - 5 | Vancouver CanucksVancouver Can |
| 14 Feb 99 | r00        | Nashville PredatorsNashville Pre | 2 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 16 Feb 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 7 - 3 | Washington CapitalsWashington Ca |
| 18 Feb 99 | r00        | New York IslandersNew York Isla | 3 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 20 Feb 99 | r00        | New York RangersNew York Rang | 6 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 22 Feb 99 | r00        | Philadelphia FlyersPhiladelphia | 2 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 23 Feb 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 1 | Arizona CoyotesArizona Coyot |
| 26 Feb 99 | r00        | Colorado AvalancheColorado Aval | 2 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 27 Feb 99 | r00        | Dallas StarsDallas Stars | 6 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 01 Mar 99 | r00        | Washington CapitalsWashington Ca | 4 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 04 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 4 | Montreal CanadiensMontreal Cana |
| 06 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 2 | Edmonton OilersEdmonton Oile |
| 08 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 1 - 3 | Colorado AvalancheColorado Aval |
| 10 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 3 | New Jersey DevilsNew Jersey De |
| 11 Mar 99 | r00        | Carolina HurricanesCarolina Hurr | 2 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 14 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 0 | Philadelphia FlyersPhiladelphia |
| 17 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 2 | Dallas StarsDallas Stars |
| 18 Mar 99 | r00        | Tampa Bay LightningTampa Bay Lig | 0 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 21 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 1 - 1 | Nashville PredatorsNashville Pre |
| 22 Mar 99 | r00        | New York RangersNew York Rang | 2 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 24 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 5 - 2 | Chicago BlackhawksChicago Black |
| 26 Mar 99 | r00        | New Jersey DevilsNew Jersey De | 5 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 28 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 1 - 1 | Buffalo SabresBuffalo Sabre |
| 29 Mar 99 | r00        | Buffalo SabresBuffalo Sabre | 4 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 31 Mar 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 4 - 6 | Ottawa SenatorsOttawa Senato |
| 02 Apr 99 | r00        | Ottawa SenatorsOttawa Senato | 3 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 04 Apr 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 4 | New Jersey DevilsNew Jersey De |
| 05 Apr 99 | r00        | Buffalo SabresBuffalo Sabre | 3 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 08 Apr 99 | r00        | Philadelphia FlyersPhiladelphia | 3 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 11 Apr 99 | r00        | Detroit Red WingsDetroit Red W | 0 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 15 Apr 99 | r00        | Boston BruinsBoston Bruins | 4 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 17 Apr 99 | r00        | Pittsburgh PenguinsPittsburgh Pe | 2 - 7 | New York IslandersNew York Isla |
| 18 Apr 99 | r00        | New York RangersNew York Rang | 1 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| |
| 22 Apr 99 | Playoff        | New Jersey DevilsNew Jersey De | 3 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 24 Apr 99 | Playoff        | New Jersey DevilsNew Jersey De | 1 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| 25 Apr 99 | Playoff        | Pittsburgh PenguinsPittsburgh Pe | 4 - 2 | New Jersey DevilsNew Jersey De |
| 27 Apr 99 | Playoff        | Pittsburgh PenguinsPittsburgh Pe | 2 - 4 | New Jersey DevilsNew Jersey De |
| 30 Apr 99 | Playoff        | New Jersey DevilsNew Jersey De | 4 - 3 | Pittsburgh PenguinsPittsburgh Pe |
| 02 May 99 | Playoff        | Pittsburgh PenguinsPittsburgh Pe | 3 - 2 | New Jersey DevilsNew Jersey De |
| 04 May 99 | Playoff        | New Jersey DevilsNew Jersey De | 2 - 4 | Pittsburgh PenguinsPittsburgh Pe |
| |
| 07 May 99 | QF        | Toronto Maple LeafsToronto Maple | 0 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 09 May 99 | QF        | Toronto Maple LeafsToronto Maple | 4 - 2 | Pittsburgh PenguinsPittsburgh Pe |
| 11 May 99 | QF        | Pittsburgh PenguinsPittsburgh Pe | 4 - 3 | Toronto Maple LeafsToronto Maple |
| 13 May 99 | QF        | Pittsburgh PenguinsPittsburgh Pe | 2 - 3 | Toronto Maple LeafsToronto Maple |
| 15 May 99 | QF        | Toronto Maple LeafsToronto Maple | 4 - 1 | Pittsburgh PenguinsPittsburgh Pe |
| 17 May 99 | QF        | Pittsburgh PenguinsPittsburgh Pe | 3 - 4 | Toronto Maple LeafsToronto Maple |