Longest NHL playoff game

Before the Red Wings and Maroons, the Bruins and Maple Leafs went to a sixth overtime period in Game 5 of the 1933 semifinals. Maple Leafs right wing Ken Doraty ...

Nine games in the NHL playoffs have gone to quadruple overtime. The next three longest games all transpired at the turn of the century, starting with the Flyers and Penguins in Game 4 of the 2000 Eastern Conference semifinals. Tied at 3-3 at the end of regulation, Ducks right wing Petr Sykora sealed the game just 48 seconds into quintuple overtime to give his team the 4-3 win. In Game 1 of the national semifinal (before conferences arrived), the Maroons hosted the Red Wings in a lengthy thriller. Before the Red Wings and Maroons, the Bruins and Maple Leafs went to a sixth overtime period in Game 5 of the 1933 semifinals. If a regular season game is tied, it goes to a five-minute overtime period where the first team to score wins the game.