Overtime in the Stanley Cup Playoffs has no equal. There is no shootout, no three-on-three, and no easy exit. There are full 20-minute periods played through until someone scores, and the kind of mayhem only hockey can provide. If you’ve ever stayed up late into the early hours to watch a playoff game, you’ve seen one of the greatest shows in all of sports.

Game 7 between the St. Louis Blues and the Winnipeg Jets in 2025 brought fans into the remembrance of how crazy these moments turn out to be. The Jets were two goals behind and had less than two minutes remaining. They tied it with seconds to spare. Two overtime periods later, they shocked the Blues and advanced. It was the edge-of-your-seat kind of hockey, but nowhere near history’s longest game. The NHL’s most extended games have stretched the limits, both human and hockey-wise. These are not games of mere length. They are stories. Legends. Brenden Morrow’s quadruple overtime game-winner in 2008, Henrik Sedin’s dagger in 2007, or Brayden Point’s marathon victory in 2020—all are forever etched into the lore of hockey. But none are the greatest.

Because there is one game that survived them all. And it began back in 1936.

Top of the mountain—the Red Wings vs. Maroons, 1936

The game between the Detroit Red Wings and the Montreal Maroons is the longest in NHL history. On March 24, 1936, the two clubs played on into Stanley Cup semifinals history in what became the stuff of legend. The game lasted 176 minutes and 30 seconds—six full overtime periods—until rookie Modere “Mud” Bruneteau finally scored the game-breaker against Montreal’s Lorne Chabot. That one goal completed what remains the NHL’s ultimate endurance test.

What makes it all the more astonishing? Each team did not score for almost three entire games’ worth of hockey. Goalies Chabot and Normie Smith stood on their heads. Smith stopped 92 shots. Fans who endured the final buzzer did not merely observe a game of hockey—they endured an event.

Interestingly enough, so was the goaltender for the second-longest game three years previously—Toronto against the Bruins in 1933. That one, which lasted 164 minutes and 46 seconds, had ended with Ken Doraty’s sixth overtime goal, which defeated the Bruins.

Modern mayhem—the overtime beasts of recent history

The classic legends take the top rankings, but contemporary games have built over time epics of their own. The Flyers vs. Penguins in 2000 is one such example—Keith Primeau scored in the fifth OT to record a 2-1 victory after 92 minutes of overtime. In 2020, the Lightning and Blue Jackets treated us to one in the bubble era. Joonas Korpisalo blocked an NHL-record 85 shots, but Brayden Point ended it in the fifth OT, taking the win for Tampa at 3-2.

Matthew Tkachuk left his mark on the carnage in 2023. His game-winning overtime goal in Game 1 against Carolina occurred just 13 seconds short of a fifth OT. It was 1:55 in the morning when the puck found its Off the Beaten Path—Record-B.

Elsewhere beyond the NHL, the World’s Longest Hockey Game in Alberta ran from February 4 to 15, 2021. That is correct—252 hours of gameplay. It was a cancer research fundraiser, and temperatures plummeted as low as -32°C. Team Cure and Team Hope scored thousands of goals and accumulated over $1.8 million in the effort.

And then there’s the notorious 2014 playoff game between the Penguins and Capitals, where 14 minutes passed without the whistle ever being blown. No stoppage, no goal, just complete and utter chaos.

Over time in playoffs—how is it different

These playoff marathons are made possible with the sudden-death format. The overtime remains at full 20-minute periods at 5-on-5, no shootout. Each intermission is 15 minutes, and the puck drops until someone scores.

The system favors resilience, determination, and depth. You aren’t looking for stars—you are looking for fourth-liners and backup goaltenders who can take the grind. And many of the most extended games in the history of the league were decided by unsung heroes.

And indeed, the Stanley Cup has been won in overtime—17 times in all, the last being Alec Martinez’s 2014 double-OT winner for the LA Kings.

These marathon games exist in hockey history not only because of the duration but because of the heart shown. Picture skating for 100+ minutes of overtime, blocking shots with the body, gasping for air on the bench—and continuing to move ahead.

That is what playoff hockey is all about. No second opportunities, no commercials, no shootouts. Just adrenaline and the pursuit of immortality. So the next playoff game you watch goes to OT, stay awake—you may just find yourself watching the next Mud Bruneteau moment. Because in the Stanley Cup Playoffs, history is not made in regulation. It’s made in overtime sessions that can never seem to end.