Greatest Stanley Cup Playoff Upsets in NHL History

The 2021 Stanley Cup Finals got off to a dramatic start as the defending champion Tampa Bay Lightning defeated upstart Montreal 5-1 in Game 1. That the Canadiens are even in this Stanley Cup Final is nothing short of astounding.   

If Montreal could somehow pull the upset, it would surely go down in history as one of the greatest in NHL history. It’s not the first time the Canadiens were involved in a Stanley Cup upset. Here’s a look at the greatest Stanley Cup playoff upsets in NHL history.

1945 Stanley Cup Semifinals – Maple Leafs vs. Canadiens

There was only the Original Six back in 1945 and the Montreal Canadiens were the best team in hockey. During the regular season, the Habs lost just eight games finishing 38-8-4. Their opponent in the semifinals, Toronto, had barely finished over .500. It was supposed to be a quick, decisive series.

It was not. Toronto would win Games 1 and 2 by scores of 1-0, and 3-2. The Canadiens did win Game 3 and 5, but the Maple Leafs would find a way to win. Toronto’s four wins in the series were all by a single goal. The Maple Leafs would go on to capture the Stanley Cup beating favorite Detroit in seven games.

2021 Canadian Division First Round – Maple Leafs vs. Canadiens

Fast-forward 76 years and the Maple Leafs and Canadiens met once again in the playoffs. This time, it was Toronto that had the more powerful team. The Leafs won the North Division – the NHL realigned all Canadian teams into the North Division because of the coronavirus – with a record of 35-14-7. Toronto had a lineup that included prolific scorers like Auston Matthews, Mitch Marner, and John Tavares. 

Toronto held a 3-1 advantage, but Montreal, behind the play of goalie Carey Price, slowly picked away at the Maple Leafs. Montreal would win three straight games, including two in Toronto, to advance to the next round.

2003 Western Conference First Round – Wild vs. Avalanche

It was the first trip to the postseason for Minnesota since entering the league in 2000. Colorado was the third seed in the West and had won the season series over the Wild. Minnesota would win Game 1, but the Avalanche would thunder back and win the next three.

The Wild would then win three straight games each by a score of 3-2. Game 6 and Game 7 would each go to overtime. Minnesota’s Andrew Brunette scored the Game 7 winner against Colorado goalie Patrick Roy, who would announce his retirement after the season.

1982 Division Semifinals – Kings vs. Oilers

Back in ’82, Uncle Rico could throw the pigskin a quarter mile and the Stanley Cup Division Semifinlals were a five-game series. The Edmonton Oilers were the best team in the Campbell Conference finishing the 1981-82 season with a record of 48-17-15. Wayne Gretzky set NHL records for goals, 92, and points, 212. 

The Los Angeles Kings made the postseason despite a regular season record of 24-41-15. The Kings went 1-5-2 against the Oilers during the regular season. One of the losses was by a final score of 10-3. L.A. had no business even being in the series with an Edmonton team loaded with Gretzky, Mark Messier, Paul Coffey, Jari Kurri, and goalie Grant Fuhr.

The teams split the first two games and Edmonton led 5-0 in the third period of Game 3. The Kings kept fighting and cut the lead to two, 5-3, with about five minutes to play. The Kings would cash in on a power play to cut it to one and then tied it with five seconds left to play after pulling goalie Mario Lessard.

When Daryl Evans scored the game-winner just two minutes into overtime, it spelled disaster for Edmonton. The loss deflated the Oilers and the Kings would win the series by taking Game 4. L.A. would lose in the next round. The Oilers would go on to the next three Stanley Cup Finals, winning two of them (’84, ’85).

2010 Eastern Conference Semifinals – Flyers vs. Bruins

The Boston Bruins finished sixth in the Eastern Conference in 2010 just ahead of seventh-place Philadelphia. The Bruins would beat Buffalo 4-2 in the quarterfinals and then take a 3-0 on the Flyers in the semis.

Philadelphia stuck with goalie Michael Leighton despite three straight losses. The Flyers would win the next three as Simon Gagne led and offense that would score 15 goals in four games. Despite tying the series at 3-3, the Flyers fell behind 3-0 in the first period of Game 7. 

Philly fought back and it would be Gagne who would score on a power play late in the third period. The Flyers won 4-3 to complete an amazing comeback.