In early years the rivalry was rather one-sided, with the Flyers being one of the NHL's best teams during the 1970s and the Penguins not catching up until selecting Mario Lemieux first overall in 1984.
The rivalry has been especially heated in recent years, as both teams have great rosters full of young, exciting talent. They have met in the playoffs six times, all since 1989, with the Flyers winning four series to the Penguins two.
In the past few seasons both teams have met in a number of heated battles, with young stars Sidney Crosby, Evgeni Malkin, Mike Richards, and Claude Giroux all trying to establish their authority.
Here are the most memorable moments from this great rivalry.