7 Biggest First-Round Upsets in NHL Playoff History, Ranked

When you think of a first-round upset, which first-round series comes to mind?

If you have no allegiance to the favourite, upsets often provide some of the most thrilling and inspiring moments in the NHL playoffs. 

I’ve whittled down an extensive list to the seven biggest first-round upsets. Hopefully, the team you support wasn’t one of the favourites. And if your team is on the list as an underdog, what a ride that must have been. 

NHL Playoffs: Best First-Round Upsets All Time

7. Sharks vs. Red Wings (1994)

It wasn’t the 18-point discrepancy in the standings that made this one of the all-time first-round upsets, but the fact that it was the San Jose Sharks’ first playoff appearance after joining the league in 1991-92. 

Igor Larionov scored 10 points to propel the Sharks to the famous victory. Goaltender Arturs Irbe enjoyed an otherworldly Game 7 performance, and Jamie Baker scored the game-winning goal with 6 minutes, 35 seconds:35 remaining in the third period.  

6. Oilers vs. Red Wings (2006) 

The Red Wings, who won the Presidents’ Trophy with 124 points, were sizable hockey odds favourites entering the clash against the Edmonton Oilers. 

The Oilers finished the season with 95 points, but ousted the Red Wings in a six-game series that included four one-goal games. Dwayne Roloson was the key variable, with the Oilers’ goaltender winning four of five starts, posting a .923 save percentage and 2.58 goals-against average (GAA).  

It was the start of a dream playoffs for the eighth-seeded Oilers, who made it to the Stanley Cup Final before losing to the Carolina Hurricanes.

5. Canadiens vs. Capitals (2010)

The Montreal Canadiens handed the Washington Capitals, the Stanley Cup odds favourite at the BetMGM online sportsbook and Presidents’ Trophy recipients, the shock of a generation.

The Canadiens were down 3-1 in the series and reeled off three straight victories. The Capitals scored once in each of those three defeats

The Canadiens finished the season 27 points behind the Capitals.

4. North Stars vs. Blackhawks (1991)

The Chicago Blackhawks won the Presidents’ Trophy with 106 points, while the Minnesota North Stars finished the regular season in 16th place, tallying just 68 points. 

That enormous disparity didn’t faze the North Stars, who didn’t even require a seventh game, winning three straight to put the final touches on the upset at home in Game 6. The North Stars demolished the Blackhawks 6-0 in Game 5 in Chicago, representing the series’ backbreaker. 

Minnesota’s momentum took it all the way to the Stanley Cup Final, where it lost to the Pittsburgh Penguins in six games. 

3. Panthers vs. Bruins (2023)

I’ll never forget this series, and I’m sure both sets of players are in the same boat for contrasting reasons. The Bruins had the best regular season in NHL history, tallying 135 points en route to the Presidents’ Trophy. 

The Florida Panthers, meanwhile, snuck into the postseason with 91 points. 

The Bruins were up 3-1 in the series and in control before the momentum shifted in Game 4 with Matthew Tkachuk’s overtime winner. 

The Panthers repeated the Game 4 feat in Game 7, winning in overtime after tying the contest with one minute to play in regulation.   

2. Kings vs. Oilers (1982)

Dubbed the Miracle on Manchester, the Los Angeles Kings were given absolutely no chance, finishing the regular season 48 points behind the Wayne Gretzky-led Oilers. 

The Kings scored six straight in Game 3, overturning a 5-0 deficit to take the series lead. The Oilers forced a decisive Game 5 in Edmonton, but the Kings prevailed with a 7-4 victory. 

While upsets are easier to pull off in a five-game series, this is an exception to that rule, considering how much of a mismatch it was on paper.

1. Blue Jackets vs. Lightning (2019)

Yet another case of a Presidents’ Trophy winner going down in the first round, but this one had even more letdown vibes. 

Tied with the 1995-96 Red Wings for the second-most wins in a regular season (62), the Tampa Bay Lightning were the formidable Cup fav

However, it was quickly apparent that the Blue Jackets were on to something special. They completed the sweep, the first and only time the Presidents’ Trophy winner succumbed in four straight in the first round.  

What Is the Biggest Upset in the Stanley Cup Final? 

In an abbreviated 48-game 1994-95 regular season, the Red Wings finished 18 points ahead of the New Jersey Devils. 

Despite the mismatch on paper, the Devils swept the high-octane Presidents’ Trophy winners in the Stanley Cup Final.