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Every veteran hockey fan knows to expect the unexpected when the Stanley Cup Playoffs roll around each year thanks to the famously unpredictable nature of the NHL postseason.
There’s something about playoff hockey that (as the kids say) “hits different,” as players have a tendency to take their game to the next level for a postseason that’s typically defined by increased levels of physicality and borderline irresponsible levels of pain tolerance that redefine “Hockey Tough.”
2023 was a textbook example of that reality thanks to the fate that befell the Bruins, who headed into the playoffs as the odds-on favorite to hoist the Stanley Cup after completing what was statistically the most dominant regular season in NHL history only to be eliminated by the Panthers in the first round.
That eighth-seeded Florida squad didn’t stop there, as the team that eked into the playoffs by clinching a wild card spot in the final week of the season was able to win the next two rounds en route to earning the right to face off against the Golden Knights in the Stanley Cup Finals.
Sportsbooks have historically erred on the side of the aforementioned unpredictability when it comes to setting lines for the Stanley Cup Finals, and that series was no exception: Las Vegas opened as a slight favorite at -105, while Florida was allowed to keep their underdog narrative going thanks to the +135 odds they were given.
Both sides headed into the Finals knowing someone was going to make history when you consider they each headed into the postseason hoping to secure the first Stanley Cup in franchise history.
However, the hypothetically even nature of the matchup meant fans will have to wait at least one more year if they want to see a team pull off the biggest upset the NHL has ever seen in the last round.
What’s the biggest upset in Stanley Cup Finals history?
The Stanley Cup was first handed out all the way back in 1893, which means it’s a bit tricky to track down the odds for every single series where it’s been up for grabs. However, we can go as far back as 1985 thanks to the data that’s been compiled by Sports Odds History.
While the NBA Finals have featured some incredibly lopsided showdowns over the decades, you can’t really say the same about the NHL’s equivalent; the 2002 Red Wings are the heaviest favorites on record (-750), but the vast majority of the other members of that group clock in at lower than -250.
The Hurricanes were listed at +525 underdogs when they faced off against Detroit in 2002, and they were only able to win a single game before watching the Red Wings celebrate their 10th title in front of the home crowd at Joe Louis Arena.
However, there are two teams who’ve managed to play spoiler to a greater degree than any other.
The first is the Devils, who headed into the 1995 Stanley Cup Finals as +200 underdogs against none other than Detriot. However, New Jersey was not only able to hold its own but win the series with ease, as it secured its first title after pulling off the sweep.
The Bruins, on the other hand, faced more of a battle when they faced off against the Canucks in 2011. Vancouver was listed at -240 compared to Boston’s +200, and it seemed like the oddsmakers had done a pretty good job after the Canucks pulled out to a 2-0 lead.
However, the Bruins were able to even up the series before ending up on the brink of elimination following a loss in Game 5. Vancouver failed to put them away on the road in Game 6 before the city they call home found itself with a riot on its hands after the Bruins capped off the miniature comeback with a win in Game 7 to match New Jersey’s achievement.
As things currently stand, those two wins mark the biggest upsets to ever unfold in the Stanley Cup Finals, but if hockey history has taught us anything, it’s likely it’s only a matter of time until another team manages to set a new bar.