The Five Biggest Upsets in NHL Playoff History

NHL’s Wildest Underdog Stories

There aren’t many sporting scenarios as competitive and compelling as the NHL’s Stanley Cup playoffs. Space on the ice isn’t much, and each player (even the goalies) has to keep their heads on a swivel because there’s always a guy wearing the other jersey right next to them. 

What is making the 2025 NHL playoffs different is that none of the four Original Six U.S.-based teams (Boston Bruins, Chicago Blackhawks, Detroit Red Wings, and New York Rangers) qualified. That’s a first, and there is also no Sidney Crosby and the Pittsburgh Penguins.

A weird regular season, but ‘weird’ has also been a phrase used to describe some of the playoff results in the history of the league.

Some of the more stunning postseason results include…

2023 Eastern Conference First Round

Having finished the regular season with 65 wins (15-of-last-16) and a league-record 135 points as well, the Boston Bruins drew a Florida Panthers team that barely squeaked into the playoffs. Boston had a 3-1 lead in the series, those ‘extinct’ Panthers refusing to read the memo. Winning the last three, Florida ended its miracle with a Game 7 overtime victory in Boston

1982 Smythe Division First Round

Edmonton ended the regular season with 48 more points than the lowly Los Angeles Kings, going into what was a best-of-five series. It was a win each as the Oilers had a seemingly insurmountable 5-0 lead in Game 3 after two periods. That was before the ‘Miracle on Manchester (avenue on which the Los Angeles Forum was located),’ as the Kings scored five goals in the final 20 minutes before a winner in overtime. LA finished off the Oilers in the fourth game to advance,

1975 First Round

While the historic New York Rangers and newbie New York Islanders both had 88 points during the regular season, there wasn’t much reason to favor Long Island in this best-of-three. However, the Isles were winners in the opener at Madison Square Garden before the Rangers authored a rout on the road. In the deciding game, just 11 seconds into overtime, J.P. Parise stunned the Manhattan faithful as the Isles dispatched the Rangers.

Four Reverse Sweeps in Stanley Cup Playoffs

1942 Finals (Toronto Maple Leafs over Detroit Red Wings), 1975 quarterfinals (New York Islanders over Pittsburgh Penguins), 2010 East semifinals (Philadelphia Flyers over Boston Bruins), and 2014 West first round (Los Angeles Kings over San Jose Sharks). Each team overcame a 3-0 deficit to win the next four.

2019 East First Round

The Tampa Bay Lightning finished with league highs in wins (62) and points (128), while the Columbus Jackets were supposed to be nothing more than cannon fodder. The result was goalie Sergei Bobrovsky and the Jackets in four, outscoring the ‘Ning, 19-8. 

Here’s a bit of a primer on the 2025 playoffs…

Who is Favored to Win the Stanley Cup?

The eight, best-of-seven opening-round series were well underway as of this writing. At the outset of the playoffs, however, odds were tight atop the board. The defending-champion Florida Panthers were 7-1 (+700) co-favorites, along with the Dallas Stars (their lone Cup was in 1999).

Right behind at 8-1 (+800) were the Colorado Avalanche and Vegas Golden Knights.

Next were the 9-1 (+900) Carolina Panthers and Edmonton Oilers. Edmonton, of course, nearly finished a historic comeback in the Finals last season, but lost Game 7 at Florida.

It’s somewhat strange that the two best-record teams, as in the Washington Capitals and Presidents’ Trophy-winning Winnipeg Jets, found themselves at 10-1 (+1000).

Odds are/were fluid (in fact they’ve changed during the first round of play) so, it’s the job of the bettor to check NHL scores and find the best time to invest.  

How Many Teams Make the NHL Playoffs?

Half of the NHL’s 32 teams make the playoffs, with eight each out of both the East and West. There’s no play-in tournament such as in the NBA; rather, the first three teams in each division (Atlantic and Metropolitan [East,] along with Central and Pacific [West]), plus two wild card teams in each conference. It’s the best of the East and the best of the West in the Stanley Cup Finals.

What NHL Team Has Never Been to the Stanley Cup? 

We need to be a bit more specific here, as in what teams have never been to the Finals of the Stanley Cup. Looking at the 32 teams in the NHL hockey schedule, those five would (alphabetically) be the Columbus Blue Jackets, San Jose Sharks, Seattle Kraken, Utah Hockey Club (former Arizona Coyotes), and Winnipeg Jets (both incarnations).

Does BetUS Offer Constant Updates on NHL Betting Lines?

Indeed. There are individual game and series odds throughout the NHL playoff bracket. Additional props are available around individual games and the length of each series, and a board associated with the biggest individual postseason award, the Conn Smythe Trophy. 

Any Final Thoughts?

Anyone who pays even marginal attention to hockey is acutely aware of the NHL playoffs.

There are spectacular games and exciting chances to make some money. Continuing to invoke the phrase ‘do your homework’ because it’s essential if you’re going to gain any advantage against the NHL playoff odds.