- The New York Islanders sparked their dynasty with a victory in the 1980 Stanley Cup Final.
- Martin Brodeur and the 1995 New Jersey Devils swept the powerhouse Detroit Red Wings as heavy underdogs.
- Tim Thomas led the 2010 Boston Bruins to a sensational upset of the favoured Vancouver Canucks.
The Stanley Cup playoffs are a gruelling test of skill, resilience, and sometimes, a little bit of puck luck. Occasionally, a team defies the odds and pulls off an upset for the ages. These moments go down in the tales of NHL lore and are a reminder that anything is possible no matter what the hockey odds might be.
Let’s explore the nine biggest Stanley Cup Finals upsets in NHL history.
| Matchup | Series Result | Year |
| New York Islanders vs Philadelphia Flyers | 4-2 | 1980 |
| Edmonton Oilers vs New York Islanders | 4-1 | 1984 |
| Montreal Canadiens vs Calgary Flames | 4-1 | 1986 |
| Edmonton Oilers vs Boston Bruins | 4-1 | 1990 |
| New Jersey Devils vs Detroit Red Wings | 4-0 | 1995 |
| Pittsburgh Penguins vs Detroit Red Wings | 4-3 | 2009 |
| Boston Bruins vs Vancouver Canucks | 4-3 | 2010 |
| Washington Capitals vs Vegas Golden Knights | 4-1 | 2018 |
| St. Louis Blues vs Boston Bruins | 4-3 | 2019 |
1980 New York Islanders +150 vs Philadelphia Flyers
Despite boasting the likes of future NHL greats Denis Potvin, Brian Trottier, and Mike Bossy on their roster, the Islanders were significant underdogs heading into the 1980 Stanley Cup Finals.
New York managed to overcome the odds and defeat the Flyers to mark the first of four consecutive Stanley Cups. If only today’s Islanders had that luck in the Stanley Cup odds. This 4-2 series victory marked the beginning of the Islanders’ dynasty.
1984 Edmonton Oilers +180 vs New York Islanders
In a classic David vs. Goliath matchup, the young Edmonton Oilers, led by Wayne Gretzky, toppled the reigning four-time champion New York Islanders in a 4-1 series victory. This win signalled the shift of NHL dominance to the Oilers, who went on to win four of the next five Stanley Cups.
1986 Montreal Canadiens +160 vs Calgary Flames
The Montreal Canadiens shocked the hockey world by defeating the star-studded Calgary Flames four games to one to capture their 23rd Stanley Cup.
37 years ago today ON THIS DAY in hockey history (May 22, 1986):
Patrick Roy picks up his 1st career playoff shutout and Claude Lemieux scores the lone goal as the @CanadiensMTL beat the Flames 1-0 in Game #4 of the 1986 Stanley Cup Final pic.twitter.com/APR5BQ5gSJ
— Vintage Hockey Showcase (@hockey_vintage) May 22, 2023
Rookie goaltender Patrick Roy shut out the Flames in Game 4 and led the Habs to glory with an unbelievable 1.92 playoff goals-against average.
1990 Edmonton Oilers +180 vs Boston Bruins
Underdogs in the 1990 Stanley Cup Finals after trading Wayne Gretzky, the Oilers managed to defeat the Boston Bruins in five games.
Glenn Anderson and Craig Simpson each potted four goals, and Oilers goalie Bill Ranford sparkled with a 1.35 goals-against average to lead the team to victory.
1995 New Jersey Devils +200 vs Detroit Red Wings
The New Jersey Devils’ sweep of the Detroit Red Wings was a defensive masterclass. The Devils employed a stifling neutral-zone trap and defused the Red Wings’ explosive offence.
With the effervescent skills of Martin Brodeur guarding the crease, New Jersey secured their first Stanley Cup and began their era of dominance.
2009 Pittsburgh Penguins +130 vs Detroit Red Wings
The Pittsburgh Penguins avenged their loss in the previous year’s Stanley Cup Finals in a thrilling rematch with the Detroit Red Wings.
Powered by Sidney Crosby’s leadership and the emergence of Evgeni Malkin, Pittsburgh defeated Detroit in seven games.
2010 Boston Bruins +200 vs Vancouver Canucks
In one of the most dramatic Stanley Cup Finals in recent memory, the Boston Bruins outlasted the Vancouver Canucks in a tense 4-3 series. Tim Thomas’s spectacular goaltending earned him the Conn Smythe Trophy as the Bruins captured their first Stanley Cup in 39 years.
2018 Washington Capitals +133 vs Vegas Golden Knights 2018
Led by Alexander Ovechkin’s rambunctious skills, the Washington Capitals overcame the expansion Vegas Golden Knights to clinch the franchise’s first-ever Stanley Cup.
The Capitals’ 2018 victory was a culmination of years of playoff disappointments.
2019 St. Louis Blues +140 vs Boston Bruins 2019
The upstart St. Louis Blues captured their first Stanley Cup in franchise history by defeating the Boston Bruins 4-3 in a hard-fought series.
In late January of that season, St. Louis sat in the basement of the NHL standings before a remarkable turnaround sparked their unlikely Stanley Cup run.
