The rivalry exists due to divisional alignment and geographic location, as both teams play in the Commonwealth of Pennsylvania.

The Flyers and Penguins met in the Stanley Cup playoffs four times in 11 years from 2008 to 2018, strengthening the rivalry.

[12] The rivalry was not as strong in earlier years, as the Penguins struggled in the NHL until the arrival of Mario Lemieux in 1984–85.

The Flyers missed the playoffs for the next five seasons, while the Penguins became an annual contender with such stars as Lemieux, Jaromir Jagr, Ron Francis, and Larry Murphy.

During that same season, the Flyers won the Eastern Conference's crown by one point in the standings, despite Pittsburgh having 49 wins to Philadelphia's 45.

[14][15] One of the most memorable moments of the rivalry occurred during the 1999–2000 season when the two teams met in the Eastern Conference Semifinals.

The rivalry between the two teams lost its luster in the years leading up to the 2004–05 NHL lockout, as the Penguins struggled on-and-off the ice, dropping to the bottom of the League standings.

[18][19] Whilst playing for Pittsburgh two years earlier, Talbot scored both goals in the Penguins' Cup-clinching Game 7 win against the Detroit Red Wings in 2009.

[18] The rivalry between the two teams briefly became an alliance late in 2011, when Commissioner Gary Bettman and the NHL began discussions for league realignment from six divisions to four.

[20] When the re-aligned conferences were unveiled later that year, both teams were placed in the eventually-named Metropolitan Division, ensuring the rivalry's continuation.

[26] In the 2019 NHL Stadium Series, set at Philadelphia's Lincoln Financial Field, the Flyers bested the Penguins in a 4–3 overtime victory,[24] rallying from a seemingly insurmountable 3–1 deficit in the final frame with two extra attacker goals.

Between these two outdoor matches, the Penguins also defeated the Flyers in their 2018 playoff clash, four games to two, following a season sweep courtesy of Pittsburgh.

Game 5 saw a 4–2 Philadelphia win, with Sean Couturier scoring the game-winning goal with just over a minute left in regulation.

Their antics reached a new high, as during game three of the 2018 playoffs, pictures of Crosby appeared in the urinals inside of Wells Fargo Center.

[27] On the other side, Penguins fans tend to simply chant, "Flyers suck," rather than singling out specific players.