One of the NHL’s most iconic duos will be back on ice in 2026–27 against the Philadelphia Flyers as Sidney Crosby and the Pens will take on the rivalry. The first game comes in Philadelphia on Sept. 30, and it will come as a reminder of the fireworks that lit up the air during their playoff clash.
The contests continued an epic arc in the 2026 Stanley Cup playoffs, when the Penguins and Flyers clashed in the first round. Philadelphia picked up six wins and ended Pittsburgh’s playoff bid and would add another gesture of drama to the long-running play-by-play between the two Philadelphia rivals. The series reinvigorated the camaraderie, the emotion and the pressure that has been a feature of meetings between the two teams in the past.
The game against the Kings holds personal significance for Crosby, as it is his first game in his NBH / NHL career. The Penguins’ captain has always been a Philadelphia problem since he joined the league in 2005. The Flyers will continue paying attention to him when playing him, as he has a 4-1 record in his career meetings.
Crosby will carry the torch once again as one of Pittsburgh’s key players, and Philadelphia will have to take advantage of its playoff success and continue in that vein. The Flyers won the confidence of the game that they can play in clutch moments with their recent strong performance in the playoffs and the Penguins will take the challenge after getting eliminated early.
The first game between them also presents a fascinating narrative to fans of the game. Crosby and the Penguins won’t step into the new season with a change-of-scene matchup, but rather against an opponent they’ve already seen play in the playoffs.
The matchup is poised to reignite in 2026–27 as the rivalry continues to ramp up, now coming together in Philadelphia as kicks are scheduled to start this new season. It will certainly have plenty of activity covering up from the first face off, but if the next chapter plays again it will be hard to tell as Crosby and Pittsburgh vs the Flyers has a history of it.
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