Top Five NHL First-Round Upsets Of The Last 20 Years

The Sharks did manage to pick up two wins in the series, but behind an eight-point series from Ryan Getzlaf and expert goaltending by a 27-year-old Jonas Hiller, who put up a .957 save percentage, 1.65 goals-against average and two shutouts, the Ducks pulled off the upset in six games.

With this series win, the Ducks became just the third team of the 2000s to beat a Presidents' Trophy winner in the first round.

4. Edmonton Oilers vs. Detroit Red Wings (2006)

During the late 1990s and early 2000s, the Detroit Red Wings were the NHL's model of consistency, entering the 2006 playoffs riding a 15‑year post-season streak and boasting three Stanley Cup wins in that span.

With a roster featuring veterans Brendan Shanahan, Nicklas Lidstrom and Steve Yzerman, along with rising stars Henrik Zetterberg and Pavel Datsyuk, Detroit dominated the regular season with a 58‑16‑8 record, securing them a second straight Presidents' Trophy.

Their first challenge was the eighth‑seeded Edmonton Oilers, a team that had barely slipped into the playoffs and lacked the star power Detroit possessed.

Despite the mismatch on paper, the Oilers quickly proved they weren't intimidated.

After Detroit took Game 1, the Oilers punched back with wins in Games 2 and 3, including a double‑overtime thriller when Shawn Horcoff assisted on Jarret Stoll's game‑winner – one of three helpers by Horcoff in the game.

Although the Red Wings tied the series the following game, Edmonton seized control and stunned the hockey world by eliminating Detroit in six games.

The Oilers carried that momentum through the Western Conference and all the way to the Stanley Cup final, ultimately falling to the Carolina Hurricanes in a tight seven‑game series.

But even without a championship, the 2005-06 Oilers remain one of the league's great underdog stories, thanks in large part to the improbable upset that launched their unforgettable run.

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3. Montreal Canadiens vs. Washington Capitals (2010)

Going into the 2010 playoffs, the Washington Capitals were riding high as the league's top team.

Just one year prior, the Capitals had reached the second round for the first time in the 2000s, and in the 2009-10 campaign, Washington excelled with an elite offensive group led by a 24-year-old Alex Ovechkin and a 22-year-old Nicklas Backstrom.

In the first round, the Capitals matched up with the unassuming Montreal Canadiens, a team that made the playoffs as the eighth seed by just a single point over the New York Rangers.

The Canadiens had no players record more than 70 points during the season, so to suggest they could beat an offensive powerhouse like the Capitals seemed unfathomable.

Montreal managed to squeeze out an overtime win in Game 1, but Washington responded with three straight victories to put the Habs on the brink of elimination.

However, Montreal had an ace in its sleeve: goaltender Jaroslav Halak.

Halak played unreal in the next three games, only allowing Washington to score once in each. In Games 6 and 7 specifically, the Slovakian netminder turned aside 94 of 96 shots to deliver the upset series win for the Canadiens.

From there, the Habs made it to the Eastern Conference final, where they lost to the Philadelphia Flyers in five games.

Despite that conclusion, their upset victory in Round 1 is all people remember, and rightfully so.

The Florida Panthers eliminated the record-breaking Boston Bruins in 2023 after being 3-1 down in the series. (Bob DeChiara-Imagn Images)

2. Florida Panthers vs. Boston Bruins (2023)

While the Florida Panthers are known today as two-time Stanley Cup champions, they just barely snuck in as the second wild-card team in the Eastern Conference in 2023.

Compared to the rest of the teams on this list, on paper, the Panthers had the toughest first-round matchup – the Boston Bruins.

The 2022-23 Bruins went a historic 65-12-5, breaking records for most points and wins in a season in NHL history.

With solid defense, a Vezina-winning season from goaltender Linus Ullmark and a breakout 113-point campaign from right winger David Pastrnak, the Bruins looked primed to win the Cup.

So when the Bruins took a 3-1 series lead after Game 4, many assumed they had the series in the bag.

They were very wrong.

The Panthers kept the series alive with an overtime-winner by Matthew Tkachuk in Game 5, and they forced a Game 7 with a 7-5 victory in Game 6.

The final game of the series was extremely close. In fact, if it weren't for a late tying goal with a minute remaining in the third period by defenseman Brandon Montour, the Bruins would have narrowly escaped this first-round series.

But with that goal and an overtime-winner from Carter Verhaeghe, the Panthers pulled off one of the biggest playoff upsets of all-time.

They made it to the Stanley Cup final that year, and they eventually won back-to-back Cup finals in 2024 and 2025.

Since their series in 2019, Sergei Bobrovsky and Andrei Vasilevskiy have won the Stanley Cup twice each. (Aaron Doster-Imagn Images)

1. Columbus Blue Jackets vs. Tampa Bay Lightning (2019)

While they didn't have the greatest record of all-time like the 2022-23 Bruins, the 2018-19 Tampa Bay Lightning were an equally formidable squad.

Finishing the regular season in a tie for the second-most wins in NHL history, the Lightning were a true powerhouse, with three players scoring more than 90 points.

One of these players, right winger Nikita Kucherov, had the best season of his career up to that point with 41 goals and 128 points, winning him the Ted Lindsay, Hart and Art Ross Trophies.

Coming into the 2019 post-season, the Presidents' Trophy winners were heavy favorites to win the Cup.

Their first step to reach that goal was a first-round bout with the Columbus Blue Jackets.

The 2018-19 Blue Jackets did feature a 27-year-old Artemi Panarin, who put up a solid 87 points, but apart from him, no one on the team even had 70 points.

It seemed unlikely that Columbus would put up much of a fight, with many fans and media alike assuming it would be a quick sweep for Tampa Bay.

When the series got underway, the total opposite occurred.

The Lightning did not look like Cup favorites, and the Blue Jackets looked like an all-star team.

The Blue Jackets outscored the Lightning 19-8 and swept them in the process.

While it could be argued that the Panthers pulled off the bigger upset in 2023, given the Bruins' record-breaking season, the Panthers went on to win two Stanley Cup championships in the following seasons, so they clearly had that 'up next' factor.

But with the Blue Jackets, their victory truly came out of nowhere. The team has failed to recapture that success since, and while the Panthers took the full seven games to beat the Bruins, the Blue Jackets didn't even let Tampa Bay get a single game.

That is why their upset sits at the top spot on this list.

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