The NHL playoffs are unlike any other time of the year for several reasons. In addition to the quality of the play on the ice and the intensity of every game, there is also the obvious difference in the rules of the game. During the regular season, games that are tied after 60 minutes go to a five-minute, three-on-three overtime period followed by a shootout. In the playoffs, they play five-on-five overtime with 20 minutes periods until somebody eventually scores and wins the game. The longer those games go on the more heartbreaking those overtime losses can be for the team that comes out on the wrong end. Here is a look at the five longest overtimes games in NHL history.
March 24, 1936 – Stanley Cup Semifinal
Detroit 1 – Montreal 0
Overtime Length: 116 minutes, 30 seconds (6th Overtime)
The Detroit Red Wings and Montreal Marooons went six overtimes in a Stanley Cup semifinal game. Detroit eventually pulled out the victory with Mud Bruneteau scoring the winner. The two teams played 116 minutes and 30 seconds, which is nearly the equivalent of three full NHL regulation games. Considering the size of goalie equipment back then it’s amazing that neither team was able to score sooner to end this game.
That win proved to be key as the Detroit Red Wins would go on to win the Stanley Cup Finals in 1936. They faced off with the New York Rangers and ended up winning the series 3-2.
April 3, 1933 – Stanley Cup Semifinal
Toronto 1 – Boston 0
Overtime Length: 104 minutes, 46 seconds (6th Overtime)
This is another example of an unbelievable game where the first and only goal wasn’t scored until nearly two full games of hockey had been played. Toronto and Boston were scoreless through eight periods when Ken Doraty finally ended this game in the sixth overtime. It’s probably no coincidence that the longest games in NHL history each included just a single goal in the game-winner.
The Toronto Maple Leafs would end up moving to the Stanley Cup Final that year but they didn’t win it. The New York Rangers actually raised the Cup that year as they won the final series 3-1.
May 4, 2000 – Eastern Conference Semifinal
Philadelphia 2 – Pittsburgh 1
Overtime Length: 92 minutes, 1 second (5th Overtime)
It took more than five decades for another NHL playoff game to reach five overtimes. The Penguins and Flyers were locked in a 1-1 tie when Keith Primeau became the hero and finally ended it with the overtime winner in the fifth extra period.
Unfortunately for both teams, neither would move on to make it to the Stanley Cup Finals that season. The New Jersey Devils ended up winning in the East while the Dallas Stars took the west. The Devils would end up winning the Stanley Cup Finals 4-2.
April 24, 2003 – Western Conference Semifinal
Anaheim 4 – Dallas 3
Overtime Length: 80 minutes, 48 seconds (5th Overtime)
Three years after the Flyers and Penguins went to five overtimes, the Ducks and Stars played four full extra periods before their Western Conference semifinal game finally ended. Petr Sykora scored the game-winning goal in that one just 48 seconds in to the fifth and final overtime.
The win proved to be an important one for the Ducks as they would go on to play in the Stanley Cup that year. They squared off with the Minnesota Wild in the Western Conference Final before moving on to face the New Jersey Devils in the Stanley Cup Final. The Devils won the series 4-3.
April 24, 1996 – Eastern Conference Quarterfinal
Pittsburgh Penguins 3 – Washington Capitals 2
Overtime Length: 79 minutes, 15 seconds (4th Overtime)
Only four games in NHL history have gone to five overtime periods. However, the 1996 Eastern Conference quarterfinal game between the Penguins and Capitals came within a minute of joining that list. Pittsburgh and Washington were tied at 0 with under a minute left in the fourth overtime when Petr Nedved ended it with the winner for the Pens. The Capitals franchise has long had playoff hiccups and this was another time that they stumbled.
The Penguins would end up winning the series and would move on to the Eastern Conference Finals before losing to the Florida Panthers.
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