Pittsburgh Penguins-Philadelphia Flyers Series Preview: Series History, X-Factors, Series Prediction

The Pittsburgh Penguins are set to renew their rivalry with the Philadelphia Flyers in the first round of the 2026 Stanley Cup Playoffs. This will be the first time that these two teams have met in the playoffs since 2018, when the Penguins won in six games. It's also the last time the Penguins won a playoff series, so it's only fitting that they'll have a chance to snap their eight-year drought against the team they last won a series against.

For a while, it looked like the Flyers were going to miss the playoffs, but they went on a massive heater down the stretch, winning 12 of their last 16 games. At one point, they were nine points out of a playoff spot in March, but got hot at the perfect time. Meanwhile, the Penguins were in a playoff spot for a good chunk of the season and finished the job against the New Jersey Devils on Apr.

9. Playoff series history The two teams have met in seven playoff series, with the Flyers winning four. Here's the full series history: - 1989 Patrick Division Finals: Flyers defeated the Penguins in seven games - 1997 Eastern Conference Quarterfinals: Flyers defeated the Penguins in five games - 2000 Eastern Conference Semifinals: Flyers defeated the Penguins in six games - 2008 Eastern Conference Final: Penguins defeated the Flyers in five games - 2009 Eastern Conference Quarterfinals: Penguins defeated the Flyers in six games - 2012 Eastern Conference Quarterfinals: Flyers defeated the Penguins in six games - 2018 Eastern Conference Quarterfinals: Penguins defeated the Flyers in six games 2025-26 Season Series Each team won two of the four games during the 2025-26 regular season.

The Flyers won the first matchup 3-2 in a shootout back on Oct. 28 before the Penguins won the next two 5-1 on Dec. 1 and 6-3 on Jan.