• Loading stock data...
Tuesday, July 15, 2025

The 10 Biggest Stanley Cup Upsets of All Time

Underdogs have had a surprising amount of success against favored teams since the 1984–1985 season. It doesn’t always take seven games for these teams to win.

Jun 12, 2019; Boston, MA, USA; St. Louis Blues center Ivan Barbashev (49) and right wing Vladimir Tarasenko (91) hoists the Stanley Cup after defeating the Boston Bruins in game seven of the 2019 Stanley Cup Final at TD Garden
Winslow Townson/Imagn Images

Since the 1984–1985 NHL season, 10 squads have defied the odds to win the Stanley Cup as underdogs. Roughly once every four years, the favorite going into the series comes out disappointed.

These teams, perhaps unexpectedly, often haven’t had to squeak out series wins in six or seven games. Data shows that among the winning underdog franchises, half claimed the Cup in just four or five games. 

The New Jersey Devils finished the 1994–1995 lockout-shortened season 5th in the Eastern Conference. In the finals, they faced off against the Western Conference top-seeded Detroit Red Wings, who were heavy favorites based on their superior records in regular-season and playoffs, where they had gone 12–2. But the Devils, +200 underdogs, swept them on the back of goaltender Martin Brodeur, outscoring Detroit 16–7.

Some series do extend to seven games, such as in 2011, when the Stanley Cup Finals featured the Boston Bruins (3rd in the Eastern Conference) against the favored Vancouver Canucks, who finished first in the Western Conference. The Bruins (+200) dropped the first two games against Vancouver, making the oddsmakers look prophetic. Yet they won, outscoring the Canucks 9–2 in the final two games.

Since back-to-back upsets in 2018 and 2019, results went as expected until 2024–2025, when the Florida Panthers overcame +105 odds to win the Stanley Cup.

Ranking the Biggest Upsets Ever

Here is the list of every upset in a Stanley Cup Finals series since the 1984–85 season, in order of betting odds entering the finals. The list was compiled using historical odds from Sports Odds History.

2011: Bruins def. Canucks in 7 /+200

1995: Devils def. Red Wings in 4 / +200

1990: Oilers def. Bruins in 5 / +180

1986: Canadiens def. Flames in 5 / +160

2001: Avalanche def. Devils in 7 / +160

2019: Blues defeated Bruins in 7 / +140

2018: Capitals def. Golden Knights in 5 / +133

2009: Penguins def. Red Wings in 7 / +130

1997: Red Wings def. Flyers in 4 / +1152025: Panthers def. Oilers in 6 / +105

Related lists:

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Ken Griffey Jr. won the 1998 Home Run Derby at Coors Field.

Players With the Most Home Run Derby Appearances

Ken Griffey Jr. had eight Home Run Derby appearances—and three wins.
Rimouski, QC - JUNE 1: Final Game of the 2025 Memorial Cup between the Medicine Hats Tigers and the London Knights on June 1, 2025, at the Colisée Financière Sun Life in Rimouski, Qc.

CHL Is Facing a ‘Pandora’s Box’ of Questions Amid NCAA Talent Departure

As players defect to college, the Canadian Hockey League won’t cede ground.
Oct 27, 2024; Philadelphia, Pennsylvania, USA; A general view of the Wells Fargo Center before game between Philadelphia Flyers and Montreal Canadiens.

New Philly Arena Will Redefine Home-Court Advantage, CEO Says

The forthcoming venue will arrive with plenty of ambition among its owners.
May 28, 2025; Oklahoma City, Oklahoma, USA; Oklahoma City Thunder forward Chet Holmgren (7) and guard Shai Gilgeous-Alexander (2) celebrates during the second quarter against the Minnesota Timberwolves in game five of the western conference finals for the 2025 NBA Playoffs at Paycom Center.

How Does the NBA Salary Cap Work?

The NBA salary cap gives teams a spending limit for their rosters.

Featured Today

May 31, 2025; Philadelphia, PA, USA; Sydney McLaughin-Levrone (USA) reacts before the women's 100m hurdles during the Grand Slam Track Philadelphia at Franklin Field
exclusive

Track’s New Money Is Running Into Old Problems

The sport’s big-money era has hit some speed bumps in 2025.
Bobbleheads are seen at Vintage Indy Sports, Tuesday, April 29, 2025 in Speedway. The local sports memorabilia store opened recently.
July 12, 2025

Baseball’s Bobbleheads Are the Center of the Collectibles Universe

Baseball’s most important keepsake drives long lines—and big business.
Jun 28, 2025; Arlington, Texas, USA; Seattle Mariners catcher Cal Raleigh (29) bats during the game between the Texas Rangers and the Seattle Mariners at Globe Life Field.
July 9, 2025

The Torpedo Bat Business Is Still Going Strong: ‘Here to Stay’

Demand for the oddly shaped bats has stayed strong across the sport.
July 6, 2025

American Celebs Want to Be Sports Owners. Soccer Is Where They Start

As U.S. team prices climb, investors set their sights abroad.
Gabby Thomas
exclusive
June 12, 2025

Grand Slam Track Cancels Los Angeles Meet As $30 Million Track Start-Up..

Sources close to Grand Slam insist money is not an issue.
June 13, 2025

What Rolapp’s NFL Exit Means—and the Top Candidates to Replace Him

NFL media boss Brian Rolapp leaves; the league hunts for his replacement.
Sponsored

Game On: Portfolio Players Stories, Brought to You by E*TRADE from Morgan Stanley

Dealmaker Jeffrey Kaplan maps the evolution of sports as an asset class
May 23, 2025

New LPGA Commissioner: Women’s Golf ‘Really Hard’ to Find on TV

Former PGA of America COO Craig Kessler will lead the tour.
Donald Trump, Nick Saban
May 22, 2025

Proposed Trump College Sports Commission May Never Happen

The White House is not sure of its plans.
May 15, 2025

PGA Championship Tees Off With Free Food, Record Hospitality Sales

General admission includes unlimited food and non-alcoholic beverages.
Allyson Felix
May 1, 2025

Allyson Felix on Olympic Pay, Nike, and Track’s Big-Money Era

Felix talked to FOS about her push to help Olympic parents and more.