The Biggest Upsets in NHL History

Every NHL fan knows the feeling when a series starts to swing away from the favourite, and the arena suddenly sounds tense instead of confident. All it takes is one hot goalie or one ugly goal, and a team that looked untouchable all season starts feeling the pressure.

This guide looks back at the playoff shocks that still get talked about years later, when an underdog walked into a mismatch on paper and flipped it on the ice. For each upset, you’ll get the backdrop that made it so surprising and the ripple effects that followed.

1971 - Montreal Canadiens vs. Boston Bruins (Quarterfinals)

In 1971, Boston entered the playoffs as the defending champion and the league’s clear powerhouse. The Bruins piled up 121 points, and Phil Esposito’s 76-goal season helped fuel a record-setting offence. Montreal slipped into the postseason and handed the net to rookie Ken Dryden, who had only a handful of NHL games to his name. What followed still sits near the top of the biggest NHL upsets.

In the quarterfinals, Dryden took over the series and helped the Canadiens beat Boston in seven games, outdueling Bruins goalie Gerry Cheevers while slowing an attack that had overwhelmed the league. Montreal kept rolling after the shocker and went on to win the Stanley Cup, despite finishing third in its division. Dryden captured the Conn Smythe as playoff MVP, then won the Calder Trophy the next season, sealing a run that turned a long shot into a champion.

1982 - Los Angeles Kings vs. Edmonton Oilers (“Miracle on Manchester”)

Edmonton arrived with a roster full of young stars and the league’s loudest offence, led by 21-year-old Wayne Gretzky, coming off a 212-point season. The Oilers finished with 111 points, and they looked built for a deep run. Los Angeles sat on the other end of the scale with 63 points, creating a massive 48-point gap in a first-round best-of-five that most people expected to end quickly.

Game 3 flipped the series into legend and earned the name “Miracle on Manchester.” Edmonton led 5-0 after two periods, then the Kings scored five straight in the third to tie it in the final seconds before winning 6-5 in overtime. Los Angeles took the series 3-2, sealing it with a 7-4 win in Game 5 in Edmonton. The Kings fell in the next round, but the upset stayed iconic because it exposed how quickly a playoff series can turn.

1991 - Minnesota North Stars vs. Chicago Blackhawks (Division Semifinals)

Minnesota limped into the 1991 playoffs with 68 points, a losing record, and a roster that looked outgunned most nights. They were 12 games under .500 and barely grabbed a postseason spot. Then they drew Chicago, the Presidents’ Trophy winner with 106 points, a team built around stars like Ed Belfour and Chris Chelios, with Jeremy Roenick in his prime. The gap felt huge, and the fact that a turnaround happened is why this series still belongs among the biggest NHL upsets.

Minnesota closed that huge gap with goaltending and team defence that stayed steady game after game, shocking the Blackhawks in six games and ultimately winning the series 4-2. They kept the run alive by taking out the St. Louis Blues, who had 105 points, then pushed all the way to the Stanley Cup Final before losing to Pittsburgh. The North Stars became the first team to eliminate the league’s top two regular-season teams in back-to-back rounds, and the run earned the “Miracle in the Land of 10,000 Lakes” label for a reason.

1993 - New York Islanders vs. Pittsburgh Penguins (Division Final)

Game 7 in Pittsburgh ended with a shocker that has left a bitter taste for Penguins fans ever since, because it turned a sure-looking run into an early exit on home turf. David Volek, who had been left out of the lineup earlier in the series, scored the overtime winner and sent the Islanders through. Goalie Glenn Healy made key saves when the pressure rose, and New York found a way to close it out, sealing one of the biggest NHL upsets in the modern playoff era.

The matchup looked one-sided from the start, as Pittsburgh, then back-to-back Stanley Cup champions, put up 119 points and entered the playoffs on a 17-game winning streak. Mario Lemieux and Jaromir Jagr led the attack, with Ron Francis adding more firepower. The Islanders had 87 points and were missing Pierre Turgeon, so most people expected Pittsburgh to cruise. New York still pushed it to seven, won Game 6 to force the decider, then stole Game 7 before losing to Montreal in the Conference Final.

1994 - San Jose Sharks vs. Detroit Red Wings (Western Quarterfinals)

San Jose entered the 1993-94 season in just its third year, and the franchise's start had been rough, with the 1992-93 team posting the worst record in NHL history. Then the turnaround hit fast, as the Sharks grabbed a playoff spot as the No. 8 seed in the West.

Waiting for them next was Detroit, a 100-point club that finished first in the conference and carried real Cup expectations behind stars like Steve Yzerman and Sergei Fedorov. San Jose had 82 points and a 33-35-16 record, so simply making the playoffs already felt like a win.

The series still went the distance, and the breakthrough came in a tense Game 7 in Detroit. San Jose lost a 2-0 lead, then refused to fold, and Jamie Baker turned a Chris Osgood mistake into the late go-ahead goal. The Sharks held on for a 3-2 win and earned the franchise’s first playoff series victory on the road. It was historic in its own right, since they became the first team since the 1975 Islanders to reach the second round in their first playoff appearance. Goalie Arturs Irbe was outstanding and San Jose carried the momentum into the next round before losing to Toronto in seven.

2003 - Mighty Ducks of Anaheim vs. Detroit Red Wings (Conference Quarterfinals)

Anaheim came in as the No. 7 seed with 95 points, and the matchup was treated as a stepping stone for Detroit. The Red Wings were the defending Cup champions with 110 points, and they held the No. 2 seed in the West. The roster was loaded with big names, and it included eight players who would become Hall of Famers in the future. Steve Yzerman and Sergei Fedorov were still prominent figures, and Nicklas Lidström held the blue line.

Anaheim swept Detroit 4-0, and every win was by one goal, showing how tight each game was. Jean-Sébastien Giguère set the rhythm in Game 1 with 63 saves in a triple-overtime win, and Detroit’s attack stayed bottled up after that. Two of the Ducks’ four wins came in overtime, and Detroit became only the second defending champion ever swept in the first round the next year. Anaheim earned its first playoff series win via a sweep, then Giguère stopped 165 of 171 shots for a 1.24 GAA and won the Conn Smythe even though the Ducks lost the Stanley Cup Final to New Jersey in seven.

2006 - Edmonton Oilers vs. Detroit Red Wings (Conference Quarterfinals)

Edmonton walked into Detroit as the No. 8 seed and walked out with one of the biggest NHL upsets of the modern era. The Oilers won the series 4-2 and finished it in Game 6 at Rexall Place, defeating Detroit 4-3 after surviving a late Detroit push. Chris Pronger played huge minutes and helped smother Detroit’s attack, while Dwayne Roloson delivered the saves Edmonton needed when the series tightened.

The result stunned because Detroit had owned the regular season, posting 124 points and winning the Presidents’ Trophy by a wide margin. That team still had proven leaders like Steve Yzerman, plus Nicklas Lidström and Brendan Shanahan, and it also had Henrik Zetterberg on the rise. Edmonton finished with 95 points, which left a 29-point gap, and Detroit’s exit made for a brutal ending to Yzerman’s final season. The Oilers carried the momentum all the way to the Stanley Cup Final, then lost Game 7 to Carolina after knocking off San Jose and Anaheim along the way.

2010 - Montreal Canadiens vs. Washington Capitals (Conference Quarterfinals)

Washington came into the 2010 playoffs as the league’s top regular-season team, and they looked built to roll. The Capitals won the Presidents’ Trophy with 121 points, and the offence was loaded, with Alex Ovechkin scoring 50 goals. Nicklas Bäckström helped lead the attack, and Mike Green powered the blue line. Montreal slipped into the bracket with 88 points as the No. 8 seed in the East, so the path to an upset pretty much required Jaroslav Halak to get hot.

That’s exactly how the series turned, even after Washington went up 3-1 and looked ready to close it out. Halak stopped 37 shots in Game 5 to keep Montreal alive, then he delivered a 53-save performance in a 4-1 win in Game 6 to force a decider. In Game 7 in Washington, he stopped 41 of 42 and the Canadiens won 2-1, becoming the first No. 8 seed to erase a 3-1 deficit and beat a No. 1 seed.

Washington closed out the series at -645 to win, and their offence had scored 300-plus goals in the regular season, yet it was shut down when it mattered most. Montreal rode the momentum into the next round and also beat the defending champion Penguins to reach the Eastern Conference Final.

2019 - Columbus Blue Jackets vs. Tampa Bay Lightning (First Round)

Tampa Bay entered the 2019 playoffs with a season that had people arguing about where they belonged among the all-time great teams. They tied the NHL record with 62 wins and finished with 128 points, which was one of the highest totals in league history and the most by any team since the mid-1990s. They finished 21 points clear of the next-best club, won the Presidents’ Trophy by a mile, and had top-end awards to match. Columbus arrived with 98 points as the No. 8 seed, and the franchise had never won a playoff series.

Then, one of the biggest NHL upsets played out in real time as Columbus swept Tampa 4-0. Game 1 set their foot when Tampa jumped ahead 3-0, then watched the Blue Jackets storm back for a 4-3 win. The Lightning never found their edge again, with Sergei Bobrovsky standing tall and Columbus’s forecheck choking off time and space, while coach John Tortorella pulled the right levers and deadline add Matt Duchene paid off.

Tampa were fully fit and had outscored Columbus 17-3 in three regular-season meetings, yet Game 4 ended with a 7-3 Blue Jackets win. Tampa did respond later with Stanley Cup wins in 2020 and 2021, but 2019 remained the standard for a first-round shock.

2023 - Florida Panthers vs. Boston Bruins (First Round)

Boston’s 2022-23 season set a new NHL standard with 65 wins and 135 points, the most in NHL history. They won the Presidents’ Trophy and looked built for a long run, powered by David Pastrnak’s 61 goals and a deep, veteran lineup. In the net, Linus Ullmark and Jeremy Swayman had just won the Jennings Trophy. Florida barely grabbed the final playoff spot in the East on the second-last day, and the Panthers finished with 92 points, which put them 43 points behind Boston, so the series opened with the Bruins as heavy favourites.

Florida still turned the series around after falling behind 3-1, winning Game 5 in overtime in Boston and taking Game 6 at home to force a decider. In Game 7, the Panthers tied it in the final minute while down 3-2, then won 4-3 in overtime on Carter Verhaeghe’s goal to end Boston’s record season on home ice. Boston had not lost three straight games all year, yet Florida handed them three in a row, with Sergei Bobrovsky finding his form mid-series as the Panthers pushed on to the Stanley Cup Final.

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