5. Mighty Ducks of Anaheim vs. Dallas Stars
> Length: 140:48
> Date: Apr. 24, 2003
> Score, winner: 4-3, Anaheim
In the Stanley Cup playoffs, it’s critical to win the first game to establish an advantage over your opponent. In their 2003 series, the Mighty Ducks and the Stars battled for well over two hours in the series opener. Two Stars, Derian Hatcher and Sergei Zubov, were on the ice for over an hour. But it was Anaheim that prevailed, with a Petr Sykora goal in the first minute of the fifth overtime. The Mighty Ducks would go on to win the series in six games.
4. Tampa Bay Lightning vs. Columbus Blue Jackets
> Length: 150:27
> Date: Aug. 11, 2020
> Score, winner: 2-1, Tampa Bay
The Tampa Bay Lightning’s road to the 2020 Stanley Cup started with one of the longest NHL games of all time. Playing the first game of their first round matchup against the Columbus Blue Jackets in the NHL’s COVID-19 bubble in Toronto, Tampa Bay tied the game at 2-2 at the beginning of the third period, then battled it out for four scoreless overtime periods. Eventually, Brayden Point scored halfway through the fifth OT to give the Lightning the win. Tampa Bay won the series in five games on their way to winning the franchise’s second Stanley Cup.
3. Philadelphia Flyers vs. Pittsburgh Penguins
> Length: 152:01
> Date: May 4, 2000
> Score, winner: 2-1, Philadelphia
Down two games to one to their in-state rival Penguins, the Flyers desperately needed a game four win in their 2000 playoff series. After trailing 1-0 for most of the game, the Flyers were finally able to score a third-period equalizer and send it to OT. Both defenses played well all game but really took it up a notch in overtime, preventing the winning goal for over 90 minutes. The Flyers’ Keith Primeau scored the winner, and Philly would go on to win the next two games to take the series.
2. Boston Bruins vs. Toronto Maple Leafs
> Length: 164:46
> Date: Apr. 3-4, 1933
> Score, winner: 1-0, Toronto
With a trip to the Stanley Cup Finals on the line, Toronto and Boston played the first 6OT game in NHL history. The offenses were held at bay for more than two and a half hours of game time. The team’s coaches even agreed to decide the game by coin flip after four overtimes because neither side seemed capable of scoring, but players refused to let it end like that. Ken Doraty finally tallied the deciding goal for the Maple Leafs in the sixth overtime, at nearly 2 a.m. Toronto would go on to lose the Finals to the New York Rangers.
1. Detroit Red Wings vs. Montreal Maroons
> Length: 176:30
> Date: Mar. 24-25, 1936
> Score, winner: 1-0, Detroit
The longest game in NHL history took place over two days in 1936, as the 6OT contest lasted until 2:25 a.m. The semifinal matchup between the Detroit Red Wings and Montreal Maroons, at over 176 minutes, was nearly three times as long as a standard game. The players were all exhausted toward the end, reportedly running on coffee and brandy. Detroit’s Mud Bruneteau finally scored a winner in the last minutes of the sixth overtime, to the relief of the players and fans alike. Some supporters were so excited they stuffed money into his jersey. This was just the first game of the series, which Detroit swept 3-0 on their way to a Stanley Cup championship.