Detroit Red Wings 1, Montreal Maroons 0 (6 OT)
1936 Stanley Cup semifinals
We have to go back 87 years for the longest game in NHL history, which mercifully ended when Detroit’s Mud Bruneteau scored at 16:30 of the sixth overtime. With 116:30 of overtime, the teams nearly played the equivalent of three full games, beginning on March 24 and ending around 2:30 a.m. on March 25. According to the NHL, Red Wings goalie Normie Smith lost 12 pounds of body weight during the game as he unofficially made 92 saves (shots were not yet an official NHL statistic).
Keep in mind that Zamboni ice-resurfacing machines were not used by NHL teams until the mid-1950s, so the rink at Montreal Forum must have been a disaster as the game wore on.
Maple Leafs 1, Bruins 0 (6 OT)
1933 Stanley Cup semifinals
Three years earlier, the deciding game of a best-of-five series between Toronto and Boston lasted so long that the morning papers began to be sold at Maple Leaf Gardens.
After a goal by the Bruins’ Alex Smith was disallowed by an offside call in the third overtime, and after another scoreless 20 minutes in the fourth, the teams’ general managers decided that the game would be decided by a coin flip. After all, the ice was extremely chopped up and the Maple Leafs were playing with numerous injured players. But players from both teams protested the decision and the game staggered on until Toronto forward Ken Doraty — all 135 pounds of him — beat Boston goalie Tiny Thompson at 4:46 of the sixth overtime and 164:46 of total play.
“We wanted to play until somebody won legitimately,” Thompson said. “It didn’t matter to us if it took all night, and it nearly did.”
Flyers 2, Penguins 1 (5 OT)
2000 Eastern Conference semifinals
The longest modern-day NHL game (92:01) — which took place two days after a single-overtime Game 3 — ended in the fifth extra period when Philadelphia’s Keith Primeau lumbered up the ice, cut inside to shake Pittsburgh defenseman Darius Kasparaitis and put one past Penguins goalie Ron Tugnutt on the short side.
Flyers center Daymond Langkow nearly ended the game just 31 seconds into the first overtime, but his shot hit the crossbar. As the overtimes piled up, things started to get a little desperate as the players tried to keep up their energy between periods.
“Usually on the road the team orders pizza for the locker room,” Primeau said. “There’s pizza for the guys, power gels, power bars, they were really popular. The trunk of those was gone, the pizza was gone. Trainers are going up to concession stands to see if there’s anything there. [The] coaches’ popcorn was eaten.”
Said referee Rob Shick: “We had the standby ref order pizza after I think it was the second or third [overtime] because we didn’t even know if we could get anything to eat after the game. In those days the teams didn’t really supply us with anything to eat. Back then we got nothing. We were lucky to get a couple rolls of tape. The problem is we had one of our standbys who’s probably the guy with the biggest appetite on our staff, and he ate three-quarters of our pizza.”
Lightning 3, Blue Jackets 2 (5 OT)
2020 Eastern Conference first round
The 2020 playoffs were played under quarantine conditions in empty arenas because of the coronavirus pandemic, and its very first game was this drawn-out affair between Tampa Bay and Columbus that ended when Lightning forward Brayden Point beat Blue Jackets goalie Joonas Korpisalo at 10:27 of the fifth overtime.
Point was so tired after 150:27 of hockey that he could barely get off the ground while trying to jump in celebration.
“Finally, one goes in. I think that’s the emotion,” he said. “Just super-excited.”
Korpisalo was beaten on the game’s final shot but set an NHL playoff record with 85 saves, snapping the mark of 73 set by the New York Islanders’ Kelly Hrudey in a four-overtime win over the Washington Capitals in the 1987 Patrick Division semifinals. The teams combined for 151 shots on goal, the most in a playoff game since that statistic began being officially tabulated in 1959-60.
Mighty Ducks 4, Stars 3 (5 OT)
2003 Western Conference semifinals
Anaheim entered Game 1 of the 2003 Western Conference semifinals having already played two overtime games — and four overtime periods — in its first-round sweep of the defending Stanley Cup champion Detroit Red Wings. It added four-plus more extra periods in its opening game against Dallas, which ended when Petr Sykora scored 48 seconds into the fifth overtime.
The Ducks led 3-1 in the second period but surrendered two goals, the last coming with just 2:47 left in regulation when a deflection by Brenden Morrow tied the score. Anaheim thought it had won the game in the third overtime when the puck went in off Steve Thomas’s leg, but the officials ruled that the net had become dislodged and waved off the goal.
Naturally, the next game also went to overtime, though the Ducks ended it after only 1:44 of extra time.
Panthers 3, Hurricanes 2 (4 OT)
2023 Eastern Conference finals
Florida’s Matthew Tkachuk barely prevented a fifth overtime Thursday night, beating Carolina goalie Frederik Andersen with 12.7 seconds left in the fourth extra period. It was the Panthers’ fifth overtime game of the playoffs, and they’ve won every single one of them.
The game appeared to end early in the first overtime, but Carolina successfully challenged a goal by Florida’s Ryan Lomberg, with the officials ruling that Colin White interfered with Anderson on the shot. The Hurricanes’ Seth Jarvis also nearly ended things later in the first extra period, but his shot rang off the crossbar.
In case you were wondering, the longest Stanley Cup finals game took place in 1990, when Edmonton defeated Boston, 3-2, on Petr Klima’s goal at 15:13 of the third overtime in Game 1.