info About this page:

Most NHL Stanley Cup Wins: Who Holds the Record?

NHL Generic Image with NHL Logo

Hockey banner image no text

Hockey Banner Image with hockey sticks

Expert Review Image

Final Thoughts

NHL Betting Expert

Rowan Fisher-Shotton

51 Articles

As you can tell, the Stanley Cup winners by year hold a rich and storied history, with some of the most iconic franchises in all sports vying for the coveted trophy every year. From the Montreal Canadiens’ record of 24 wins to the Las Vegas Golden Knights winning their first-ever Stanley Cup in 2023, the competition remains fierce and captivating.

Even though no Canadian franchise has lifted the trophy since 1993, in the unpredictable world of hockey, one is destined to reclaim the throne in the years to come. So, as the puck drops for the upcoming 2024 NHL season, fans worldwide eagerly await the triumphs and tribulations of the pursuit of the illustrious Stanley Cup.

More info on arrow

FAQs About NHL Stanley Cup Winners

Even though we thoroughly discussed the different Stanley Cup winners, several questions remain unanswered. Here are some of the most frequently asked questions about the Stanley Cup and its winners:

What is the Stanley Cup?

The Stanley Cup is the ultimate trophy for ice hockey and the oldest trophy still awarded in North America. The Cup is awarded to the team that wins the Stanley Cup Finals and is considered the champion of the NHL season.

Who has won the most NHL Stanley Cups?

The team with the most NHL Stanley Cup wins is the Montreal Canadiens. The franchise has won a total of 24 Stanley Cups, 23 of which came after the NHL took control of the Stanley Cup competition.

Who has lost the most Stanley Cups?

The team with the most losses in the Stanley Cup Finals is the Boston Bruins. Even though the franchise is in the top 5 teams with the most Stanley Cup wins, with 6 trophies, it has participated in a whopping 20 Finals. This means that the Bruins have lost the Stanley Cup 14 times.

Which teams have won the most Stanley Cups?

The number one team with the most Stanley Cups is the Montreal Canadiens, with 24 trophies. The top 5 Stanley Cup winners list includes the Toronto Maple Leafs (13), Detroit Red Wings (11), Boston Bruins (6), and Chicago Blackhawks (6).

Has any NHL team ever won multiple Stanley Cups in a row?

Several NHL teams have won two or more consecutive Stanley Cups. The Toronto Maple Leafs have managed a three-win streak twice in their history, whereas the New York Islanders have won it four times in a row. However, the longest Stanley Cup win streak goes to the Montreal Canadiens, who won five consecutive trophies from 1956 to 1960.

When was the Stanley Cup first awarded?

The Stanley Cup has a long history of over 130 years behind it. It was first awarded in 1893 to the Montreal A.A.A. and its affiliate club, the Montreal Hockey Club, for winning the Amateur Hockey Association of Canada league. When the NHL gained control of the Stanley Cup, the first team to win it was the original Ottawa Senators franchise in 1927.

How are the Stanley Cup playoffs structured?

The Stanley Cup playoffs consist of 16 teams and are carried out in four rounds. To reach the playoffs, a team must be in the top three of its division or one of the next two highest-placed teams from each Conference. Each playoff matchup is a best-of-seven series, and the team that reaches four wins first wins the series.

Who was the first team to win the Stanley Cup?

The first-ever team to win the Stanley Cup was the Montreal Hockey Club in 1893. The team was affiliated with the Montreal Amateur Athletic Association and was awarded the trophy as the winner of the Amateur Hockey Association of Canada.

More NHL Guides

We know how much our readers love Hockey and the NHL. That’s why we keep enriching our content with guides and topics that interest you the most.

6+ Years of Experience in NBA and NHL Betting
Rowan Fisher-Shotton Sports Betting Journalist at GambleOntario photo

Sports Betting Journalist

Rowan Fisher-Shotton


51 Articles

Rowan is a highly accomplished sports betting journalist with a proven track record of over 6 years in the sports media industry. He is widely recognized for his insightful coverage and thought-provoking commentary on major leagues like the NBA, NFL, and NCAA.

Expert On: NHL Betting NBA Betting Sports Betting Odds
More info on Rowan Fisher-Shotton arrow

Facts checked by