50. Philadelphia Flyers beat Pittsburgh Penguins in 5 OT
Kicking off the list is a beautiful if not long night during the 2000 Eastern Conference semi-finals against the Pittsburgh Penguins. The Philadelphia Flyers were down 2-1 heading into Game 4 and needed a win to stay in the race. The two teams always had a storied history and it was no different in 2000. The game ended up being the third longest game in NHL history as the two battled it out in overtime. After tying it up on their 17th power play, the Flyers entered a long night that would see it end in a victory.
The five overtimes last 92 minutes of play and it would see the Flyers and Penguins take turns on offensive dominance. Flyers’ Daymond Langkow made an attempt in the first overtime to score but the puck bounced off the crossbar. Pittsburgh dominated the second overtime and almost scored but the puck missed and bounced off the right post. Third overtime saw three powers plays yet no one could managed to score on them. The agony finally ended when Keith Primeau scored the game winning goal in the fifth overtime. The puck went down the right boards and the wrister went right past Penguins goaltender Ron Tugnutt, putting the Flyers up 2-1. It would be one of the biggest highlights of the series.
Next: Number 49: Legion of Doom