Saturday begins what will be Round Eight of the Pittsburgh Penguins and Flyers post-season tussles. This is the first time they have clashed in the playoffs since 2018, but it could be the start of a new chapter in this heated rivalry, as both teams are on the rise. While everyone counts down the seconds until puck drop, let’s prepare you for the series by looking back at the storied history of this cross-state rivalry.

This rivalry began in 1967 when both teams entered the league as part of the “Expansion Six.”

The teams met for the first time on Oct. 19, 1967, in Philadelphia, where the Flyers prevailed 1-0. Losing was a recurring theme for the flightless birds when they traveled East. The Penguins actually went 15 consecutive seasons without winning in Philadelphia. Between January 20, 1974, and February 2, 1989, the Penguins compiled an almost unfathomable record of 0-39-3 in their trips to the old Philadelphia Spectrum.

Led by Mario Lemieux, the Penguins turned things around in the late 1980s, and the rivalry intensified. The two teams met in the 1989 Patrick Division Final in a series that went seven games. In Game 5 of the series, Lemieux scored five goals and recorded an astounding eight points in a 10-7 win. Despite Lemieux’s heroics, the lasting memory of this game was Flyers goaltender, and former Penguins GM, Ron Hextall angrily chasing Penguins forward Rob Brown around the ice after he had scored the Penguins’ ninth goal. Game 5 was Pittsburgh’s last victory in the series; however, as Flyers back-up goaltender, and future Penguin, Ken Wregget stole the series with a stellar performance in Game 7 at Pittsburgh.   

The Penguins and Flyers met in the playoffs again in 2000, which produced this tidbit from Late Penguins head coach Herb Brooks speaking about Flyers defenseman Luke Richardson after he shot a puck from close range at Penguins defenseman Bob Boughner, while he wrestled with Flyers forward Keith Jones, “I’d go back in his family tree. Maybe he’s a direct descendant of the guy that shot Jesse James in the back. You know, the coward that shot Jesse James in the back. It must be in his family tree.”   

That same series also produced one of the most memorable playoff games in NHL history. On May 25, 2000 (the game began on May 24) Keith Primeau scored in the fifth overtime to tie the series at two. The defeat was so crushing that the Penguins never won another game in the series.   

The Penguins fell on hard times after the 2000-01 season, and the rivalry died a bit as the Flyers remained a power in the Eastern Conference, but when Sidney Crosby arrived in 2005, the hatred renewed. On Nov. 16, 2005, Philadelphia defenseman and apparent part-time dentist, Derian Hatcher went to work on the rookie Crosby’s teeth, breaking three of them with his stick.

The fans of Philly thought Crosby was diving, and head coach Ken Hitchcock accused him accordingly (though it was hard to ignore Crosby’s missing teeth) and every trip back to Philadelphia since has produced relentless booing and less than “playful” banter from the crowd.   

The rookie got the last laugh that night as he scored the game-winner in overtime with just under a minute left and has been getting the last laugh ever since. He is the NHL’s all-time leader in points and goals against the Flyers, amassing 60 goals and 79 assists (139 points) in 93 regular-season games. He has also added 15 goals and 21 assists (36 points) in 23 postseason games against them.

In Crosby’s second season, the Penguins defeated the Flyers in all eight meetings, a record that will probably never be broken since there are only three or four matchups per season. Despite the Flyers losing all eight games, the Flyers were improving in parallel with the Penguins, and the rivalry reached white-hot levels in 2008 and 2009.

In 2008, the Penguins beat the Flyers in the Eastern Conference Finals (4-1) and the Penguins prevailed again in the 2009 Eastern Conference Semifinals (4-2), on their way to winning the Stanley Cup.

The 2009 series was the famous Max Talbot vs. Daniel Carcillo fight in which Talbot shushed the Flyers crowd and the Penguins then rallied from a 3-0 deficit to clinch the series with a 5-3 win.

Of course, there was also the 2012 Eastern Conference Quarterfinals. During that bizarre and fight-filled series in which the potential Penguins dynasty seemed to unravel, the teams combined for 56 goals in the six-game series, including 10 by the Penguins in Game 4 at Philadelphia. However, the Flyers eventually won the series four games to two.

The last time these two teams clashed in the playoffs was in Round 1 of the 2018 playoffs, a series the Penguins won in six games before losing to the eventual Stanley Cup champion Washington Capitals in the second round.

In fact, that was the last time the Penguins and Crosby won a playoff series.

While the Flyers hold the historical post-season series advantage 4-3, the Penguins have won three out of the last four playoff meetings. However, this series is a bit different from some of those heavyweight battles of the past. Both teams are returning to the playoffs after extended droughts. For the Penguins, it is their first playoff appearance since the 2022 postseason, and for the Flyers, it is their first since the 2020 playoffs.

When these teams meet, a few wild moments always follow, and you can bet that it will only add to the lore of what has been one of the NHL’s best rivalries since it began nearly 60 years ago.

Tags: 2026 stanley cup playoffs Jaromir Jagr Mario Lemeuix Max Talbot Philadelphia flyers Pittsburgh Penguins Sidney Crosby Vince Comunale

Categorized:NHL Playoffs Penguins Playoffs