The 2021-22 National Hockey League regular season is coming to a close on April 29, which is when 16 teams will start their playoff journey in hopes of lifting the Stanley Cup.
The playoffs are also riveting for another reason: overtime.
Overtime play in the postseason is vastly different from the regular season, which has led to the longest games in NHL history.
Before diving into the five longest contests, here’s a brief explainer of the league’s overtime rules:
How long is overtime during the NHL regular season?
A standard NHL game is 60 minutes long divided into three 20-minute periods. If a regular season game is tied, it goes to a five-minute overtime period where the first team to score wins the game. If no team scores in that duration, the game is decided by a shootout.
How long is overtime during the NHL playoffs?
In the playoffs, overtime periods are 20 minutes long, with the first team to score winning the game. However, if the game remains tied after 20 minutes, another 20-minute overtime period will start. This continues until a team nets a goal.
What are the longest games in NHL history?
With the rules explained, the five longest games in NHL history have all occurred in the postseason. Each game needed at least five overtime periods to be decided, but two of them needed six:
Detroit Red Wings at Montreal Maroons, 1936: 6 OT
The longest game in NHL history happened all the way back in 1936. In Game 1 of the national semifinal (before conferences arrived), the Maroons hosted the Red Wings in a lengthy thriller. Detroit right wing Mud Bruneteau scored after 16:30 in the sixth overtime period, giving the Red Wings a 1-0 win and a 1-0 series lead. They would eventually sweep Montreal in three games en route to winning the Stanley Cup.
Total length: 176:30
Boston Bruins at Toronto Maple Leafs, 1933: 6 OT
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 sent Toronto to the finals after scoring 4:46 into the sixth period to give his squad the 1-0 win and a 3-2 series win. Toronto, however, fell in the national final.
Total length: 164:46
Philadelphia Flyers at Pittsburgh Penguins, 2000: 5 OT
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. The game was tied 1-1 until Flyers center forward Keith Primeau broke the stalemate after 12:01 played during the fifth overtime period. Primeau’s goal tied the series at 2-2, and the Flyers went on to win the dreaming two games to reach the Eastern Conference final, where their run ended.
Total length: 152:01
Columbus Blue Jackets at Tampa Bay Lightning, 2020: 5 OT
This game is the most recent game to have such a long finish time. In Game 1 of the first round in the East, the Blue Jackets and Lightning got off to an enthralling start. After 10:27 in quintuple overtime, Lightning center forward Brayden Point secured the puck after a deflection and shot it in from distance. Tampa Bay would go on to win the Stanley Cup that year.
Total length: 150:27
Mighty Ducks of Anaheim at Dallas Stars, 2003: 5 OT
The fifth longest game in NHL history came in 2003 when the Ducks battled the Stars in Game 1 of the Western 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. Anaheim’s run that season ended in the national final.
Total length: 140:48
How many NHL games went to quadruple overtime?
Nine games in the NHL playoffs have gone to quadruple overtime. The most recent one came in 2008 when the Stars got a 2-1 win against the San Jose Sharks in Game 6 of the Western Conference semifinals.