The Stanley Cup is the ultimate prize in professional ice hockey. As the championship trophy for the National Hockey League (NHL), having your name engraved on the Stanley Cup is the pinnacle of success in the sport. But which NHL franchise has won the most Stanley Cup championships over the long history of the league?
Quick Facts
- The Montreal Canadiens have won the Stanley Cup 24 times, more than any other NHL team.
- The Toronto Maple Leafs rank second with 13 Stanley Cup wins.
- The Detroit Red Wings are third with 11 Cup victories.
- The Boston Bruins and Chicago Blackhawks are tied for 4th with 6 championships each.
- The Pittsburgh Penguins and Edmonton Oilers have each won 5 Cups.
As those quick facts illustrate, the Montreal Canadiens are far and away the NHL’s greatest dynasty, having double the number of Stanley Cup wins as their next closest competitor. The Canadiens dominated during the early decades of the league’s existence, racking up championship after championship. But numerous franchises have climbed the mountain to hoist hockey’s holy grail over the 100+ year history of the NHL.
The Early NHL Dominance of the Montreal Canadiens
The Montreal Canadiens entered the NHL in its inaugural 1917-18 season, and it did not take them long to establish themselves as the league’s first powerhouse. They won their first Stanley Cup in 1924, defeating the Calgary Tigers of the Western Canada Hockey League. This started a run of success that is unmatched in NHL history. Between 1924 and 1960, the Canadiens won a staggering 16 Stanley Cups.
Some key stats and facts about Montreal’s dominance:
- They won 5 straight Cups from 1956 to 1960, still the longest championship streak in league history.
- Between 1951 and 1979, they missed the playoffs only once.
- Hall of Fame players like Maurice “Rocket” Richard, Jean Beliveau, and Doug Harvey led the way.
- They had legendary coaches like Dick Irvin, Toe Blake, and Scotty Bowman behind the bench.
The Canadiens took advantage of being the only NHL team in Canada’s largest city during this era. They were able to sign the best French Canadian players and build a professional hockey empire around this core. This early period of prolonged excellence firmly established Montreal as the NHL’s marquee franchise.
Canadiens’ Stanley Cup Championships (1916-1979):
| Year | Opponent | Result |
| 1924 | Calgary Tigers | Won 3-0 |
| 1930 | Boston Bruins | Won 2-0 |
| 1931 | Chicago Black Hawks | Won 3-2 |
| 1944 | Chicago Black Hawks | Won 4-0 |
| 1946 | Boston Bruins | Won 4-1 |
| 1953 | Boston Bruins | Won 4-1 |
| 1956 | Detroit Red Wings | Won 4-1 |
| 1957 | Boston Bruins | Won 4-1 |
| 1958 | Boston Bruins | Won 4-2 |
| 1959 | Toronto Maple Leafs | Won 4-1 |
| 1960 | Toronto Maple Leafs | Won 4-0 |
| 1965 | Chicago Black Hawks | Won 4-3 |
| 1966 | Detroit Red Wings | Won 4-2 |
| 1968 | St. Louis Blues | Won 4-0 |
| 1969 | St. Louis Blues | Won 4-0 |
| 1971 | Chicago Black Hawks | Won 4-3 |
| 1973 | Chicago Black Hawks | Won 4-2 |
| 1976 | Philadelphia Flyers | Won 4-0 |
| 1977 | Boston Bruins | Won 4-0 |
| 1978 | Boston Bruins | Won 4-2 |
| 1979 | New York Rangers | Won 4-1 |
Passing the Torch to New Dynasties
While the Canadiens dominated the first six decades of NHL action, new franchises eventually emerged to challenge Montreal for supremacy. In the 1980s, the New York Islanders forged their own dynasty, winning 4 consecutive Cups from 1980-1983. Those talented Islanders squads dethroned Montreal as champions, signalling a passing of the torch.
Here are some other franchises that rose to prominence after the Canadiens’ stretch of dominance:
Edmonton Oilers
- Won 5 Cups between 1984-1990 led by Wayne Gretzky and Mark Messier.
- Appeared in 7 finals in 9 years during the Gretzky era.
- Reemerged to win another Cup in 2006 behind Chris Pronger and Bill Guerin.
Pittsburgh Penguins
- Won back-to-back Cups in 1991-1992 powered by Mario Lemieux.
- Won 3 Cups from 2009-2016 led by Sidney Crosby and Evgeni Malkin.
- Established themselves as one of the strongest modern NHL franchises.
Detroit Red Wings
- Stacked with Hall of Famers like Steve Yzerman and Nicklas Lidstrom.
- Won 4 Cups between 1997-2008.
- Appeared in 6 finals in 12 years during their modern dynasty.
While none of these teams have yet matched Montreal’s total Cup wins, they began closing the gap by establishing their own sustained runs of excellence post-1980. This competitive balance is healthy for the NHL, compared to the Canadiens having little challengers in previous eras.
The Leafs, Bruins, Blackhawks, and Rise of American Hockey
In addition to the Canadiens and the aforementioned 1980s-onward dynasties, four Original Six franchises have also amassed a significant amount of Stanley Cup wins over the years. These historic teams keep the Montreal dynasty honest and represent the foundations of the NHL.
Toronto Maple Leafs – 13 Cups
- Last Cup win came in 1967, the longest active drought in the league.
- Won 3 straight Cups from 1947-1949 and another 3 from 1962-1964.
- Hockey-obsessed fanbase desperate for another championship.
Detroit Red Wings – 11 Cups
- Back-to-back champions in 1954 and 1955.
- Won 3 Cups in 6 seasons from 1997 to 2002.
- Haven’t won since 2008 but remain a perennial playoff contender.
Boston Bruins – 6 Cups
- Bobby Orr led them to Cup wins in 1970 and 1972.
- Won in 2011 behind Tim Thomas’ brilliance in goal.
- Lost in 2013 and 2019 Finals, still chasing another title.
Chicago Blackhawks – 6 Cups
- Recent 3 Cups came in 2010, 2013, and 2015.
- Powerhouse teams led by Jonathan Toews, Patrick Kane, and Duncan Keith.
- Won first Cup in 1934 behind legend Eddie Shore.
Beyond the Original Six teams, the expansion era has seen American hockey blossom in cities like Philadelphia, Los Angeles, Pittsburgh, and Anaheim. The league continues moving beyond its Canadian roots.
Here are some notable U.S. teams:
Philadelphia Flyers
- The “Broad Street Bullies” won back-to-back Cups in 1974 and 1975.
- Legendary players like Bobby Clarke, Bill Barber, and Bernie Parent.
- Reached Stanley Cup finals in 1980, 1985, 1987, and 2010.
New York Islanders
- Won 4 straight championships from 1980-1983.
- Legends included Mike Bossy, Bryan Trottier, Denis Potvin.
- Collapsed in early 1990s but are rebuilding towards another run.
Los Angeles Kings
- Won their first Cup titles in 2012 and 2014 behind Jonathan Quick.
- Wayne Gretzky brought excitement and scoring records in 1980s and 90s.
- Remain the lone California team to hoist the Cup.
The NHL has undoubtedly expanded its footprint and popularity across the United States since the 1967 expansion. American teams have now won recent Cups and carved their own stories alongside the league’s Canadian roots.
Recent Stanley Cup Trends
In the salary cap era that began post-lockout in 2005, the Stanley Cup has been awarded to a diverse set of franchises. Repeating as champions has proven difficult with the increased parity across the league. Here are some notable trends in Cup wins over the past 15 years:
- No team has won consecutive Cups since the 1997-98 Red Wings.
- 8 different franchises have hoisted the Cup during this period.
- The Kings (2012, 2014) and Penguins (2009, 2016) have won multiple Cups.
- American teams have won 11 of the last 15 Cups.
- No Canadian team has won since Montreal in 1993 – the longest Cup drought ever for Canadian teams.
The salary cap and free agency rules have given more clubs a chance at winning the Cup. While dynasties like the 80s Oilers and Islanders have become rare, the competitiveness and unpredictability is great for the NHL. As they say, the Cup is the hardest championship to win in sports!
Recent Stanley Cup Winners (2006-2018):
| Year | Winning Team | Losing Finalist |
| 2006 | Carolina Hurricanes | Edmonton Oilers |
| 2007 | Anaheim Ducks | Ottawa Senators |
| 2008 | Detroit Red Wings | Pittsburgh Penguins |
| 2009 | Pittsburgh Penguins | Detroit Red Wings |
| 2010 | Chicago Blackhawks | Philadelphia Flyers |
| 2011 | Boston Bruins | Vancouver Canucks |
| 2012 | Los Angeles Kings | New Jersey Devils |
| 2013 | Chicago Blackhawks | Boston Bruins |
| 2014 | Los Angeles Kings | New York Rangers |
| 2015 | Chicago Blackhawks | Tampa Bay Lightning |
| 2016 | Pittsburgh Penguins | San Jose Sharks |
| 2017 | Pittsburgh Penguins | Nashville Predators |
| 2018 | Washington Capitals | Vegas Golden Knights |
Which Team is the Greatest NHL Dynasty?
Given everything we’ve examined, which single NHL franchise deserves to be called the greatest dynasty in league history? While there are several worthy candidates, the mantle still belongs to the Montreal Canadiens. Here’s the rationale:
- Their 24 Stanley Cup wins is 10 more than the next best team.
- They won 5 straight Cups from 1956-1960, the longest championship streak ever.
- The Canadiens won 16 titles between 1924-1979 compared to the Maple Leafs’ 13 over their entire history.
- Montreal only missed the playoffs once from 1951-1979, a run of sustained dominance that will never be matched.
- Legends like Richard, Beliveau, Lafleur, Harvey defined generations of Canadiens excellence.
No North American pro sports team can match the Canadiens’ resume of championship consistency and longevity at the very top. The “Flying Frenchmen” established a dynasty that remains hockey’s gold standard today. While the modern NHL may be more competitive, Montreal’s place in history is cemented with 24 Stanley Cup banners flying proudly from the rafters of the Bell Centre. All dynasties and champions that follow are measured against their looming legacy of success.
Conclusion
In the century-long history of the NHL, the Stanley Cup has been won by storied franchises and passed between emerging dynasties. But no team has dominated professional hockey like the early editions of the Montreal Canadiens, winning a record 24 championships. The Habs ruled the league for decades, establishing the blueprint for building a perennial powerhouse team. While the NHL’s competitive balance has increased over the years, the Canadiens’ mark on history remains indelible. New champions are crowned annually, but no dynasty has yet to truly surpass Montreal’s long-standing run of sustained excellence and Cup dominance. For the foreseeable future, the Canadiens remain hockey’s greatest dynasty.
