The Philadelphia Flyers have dominated their first-round series against the Pittsburgh Penguins, winning the first three games of the 2026 Stanley Cup Playoffs. However, despite having two chances to eliminate their in-state rivals, they have failed to close out the series. Game 5 is set for Wednesday, where the Flyers will look to finally finish the job.

After falling behind 3-0, the Penguins rallied with victories of 4-2 and 3-2 in Games 4 and 5, respectively. This comeback has been fueled by Kris Letang, who scored pivotal goals in both games, showcasing his experience and skill at 39 years old.

Historically, both teams are familiar with playoff comebacks. The Penguins lost a 3-0 series lead in 1975, while the Flyers famously overcame the same deficit against the Boston Bruins in 2010.

In addition to the Flyers and Penguins matchup, two other first-round series are tied at 2-2. The Tampa Bay Lightning and Vegas Golden Knights both achieved crucial Game 4 victories on the road and will be returning home to face the Montreal Canadiens and Utah Mammoth, respectively.

Key players to watch for prop betting include:

• Brandon Hagel (Lightning): Anytime goal scorer (+145, FanDuel) – Leads the playoffs with six goals.
• Sidney Crosby (Penguins): 1+ assists (-140, DraftKings) – Known for his playoff performance against the Flyers.
• Lawson Crouse (Mammoth): Over 0.5 points (+110, BetMGM) – Has been consistent in contributing offensively.

As the playoffs intensify, all eyes will be on these matchups and the standout players who could tip the balance.