The Stanley Cup is the ultimate prize in professional hockey. As the championship trophy for the National Hockey League (NHL), having your name engraved on the Cup is the pinnacle of success. So which NHL franchise has enjoyed the sweet taste of victory the most times in their history?
The Top 5 Stanley Cup Winningest NHL Teams
Here are the NHL teams with the most Stanley Cup wins:
| Team | Number of Cup Wins |
|---|---|
| Montreal Canadiens | 23 |
| Toronto Maple Leafs | 13 |
| Detroit Red Wings | 11 |
| Boston Bruins | 6 |
| Chicago Blackhawks | 6 |
As the table shows, the Montreal Canadiens are far and away the leader, having hoisted Lord Stanley’s Cup a remarkable 23 times. The Toronto Maple Leafs rank second with 13 titles, while the Detroit Red Wings come in third with 11. The Boston Bruins and Chicago Blackhawks are tied for the fourth most Stanley Cup wins, with 6 apiece.
A Closer Look at the Winningest Teams
Montreal Canadiens
As one of the NHL’s “Original Six” franchises, the Montreal Canadiens have one of the longest and richest histories in hockey. Based in the hockey-crazed province of Quebec, the Habs won their first championship in 1916, before the NHL existed, when they captured the National Hockey Association (NHA) title. Once the NHL launched for the 1917-18 season, Montreal wasted no time in earning its first Stanley Cup, sweeping the Pacific Coast Hockey Association’s Seattle Metropolitans in the 1918 final.
The Canadiens went on to dominate the early NHL era, capturing six Cups between 1924 and 1931. Powered by superstars like Howie Morenz, Aurele Joliat and goaltender George Hainsworth, Montreal possessed perhaps the most fearsome offensive attack in hockey.
After winning only one Cup in the 1930s and just two over the next two decades, the Canadiens began another extended run of dominance in the 1950s. Between 1951 and 1960, innovative general manager Frank Selke built a mini-dynasty led by legendary talents Maurice “Rocket” Richard, Jean Beliveau, Doug Harvey, Bernie “Boom Boom” Geoffrion and Jacques Plante. The Habs won six championships in that 10-year span.
The Richard riot in 1955 threatened to derail Montreal’s success after the NHL suspended Richard for the rest of the season following a violent stick-swinging incident. Canadiens fans unleashed their fury, rioting and causing extensive damage around the Montreal Forum and downtown area. But the team rallied to reach the Cup final that spring before falling to the Red Wings.
The 1976-79 Canadiens rank among the greatest NHL dynasties ever assembled. With eight future Hall of Famers including Guy Lafleur, Larry Robinson, Ken Dryden, Serge Savard and coach Scotty Bowman, Montreal played an up-tempo, electrifying style that resulted in four consecutive championships. That run established the Habs as hockey’s preeminent franchise.
Montreal’s last Stanley Cup (their 23rd) came in 1993, when Patrick Roy backstopped the club past Wayne Gretzky’s L.A. Kings. The nearly three decades since that latest title have been trying ones for Canadiens fans, but the team’s glorious history remains intact.
Toronto Maple Leafs
Although Montreal holds the overall league record for Cup titles, no team has won more during the post-expansion NHL era than the Toronto Maple Leafs. All 13 of Toronto’s championships came prior to 1967, when the league doubled in size from six teams to 12. But the Leafs accumulated their collection of banners impressively nonetheless.
Like the Canadiens, Toronto began play in 1917-18 as one of the NHL’s charter franchises. Early superstars like Babe Dye, Ace Bailey and Hap Day helped lead the Leafs to their first Cup in 1918. Toronto emerged as the class of the league in the 1920s, winning four titles between 1922 and 1932.
Legendary owner Conn Smythe took control of the team in 1927 and oversaw another Maple Leafs dynasty in the ’40s. With Hall of Fame talents like Syl Apps, Ted Kennedy, Turk Broda, Max Bentley and Bill Barilko, Toronto hoisted the Cup six times between 1942 and 1951. Smythe would build Maple Leaf Gardens in 1931, which served as the team’s home arena until 1999.
The Maple Leafs went through a long drought after ’51, failing to win it all through the rest of the Original Six era. But when the NHL finally expanded in 1967, giving weaker teams new chances to contend, Toronto took advantage. Behind a roster led by Dave Keon, Frank Mahovlich, Johnny Bower, Tim Horton and Red Kelly, the Leafs bested their expansion brethren to claim Cups in 1962, 1963, 1964 and 1967.
Since the 1967 victory, which came on home ice against Montreal, the Maple Leafs have yet to return to hockey’s summit. Toronto came agonizingly close in 1993, reaching the conference finals before falling to the L.A. Kings in a seven-game classic. Generations of Leafs fans have waited patiently since then for the franchise’s 14th Stanley Cup banner to be raised to the rafters.
Detroit Red Wings
For the first half-century or so of their existence, the Detroit Red Wings struggled to find much success. Nicknamed the “Dead Wings” during the 1930s and 40s due to their stretch of futility, Detroit failed to win a single Cup between their inaugural season of 1926-27 and the early 1950s.
But once the Red Wings finally broke through, an avalanche of banners and championships followed. In a span of just over 40 years from 1950 to 1997, Detroit emerged as the NHL’s marquee U.S.-based franchise, hoisting the Cup an astounding 11 times.
The Red Wings ended their title drought in epic fashion in 1950, needing all seven games to outlast the New York Rangers in the final. Detroit nearly repeated in ’51 before losing in seven to Toronto. But in 1952, the Wings celebrated their first of back-to-back Cup wins, led by star forwards Ted Lindsay, Sid Abel and Gordie Howe, a.k.a. “The Production Line II.”
Howe would go on to serve as the face of the franchise for the next three decades, competing until the age of 52. Though the Cups dried up somewhat after 1955, Detroit remained competitive throughout the 1960s behind Howe, Alex Delvecchio, Norm Ullman and goaltender Roger Crozier.
But starting in the 1990s, Detroit began an incredible run of excellence that has yet to be matched by any U.S. team in NHL history. Riding the goaltending of Terry Sawchuk and stellar defense, the Red Wings ended a 42-year title drought in 1997. It sparked a mini-dynasty that saw Hall of Fame talents like Steve Yzerman, Nicklas Lidstrom and Sergei Fedorov lead Detroit to Cups in 1998, 2002 and 2008.
The past decade-plus has been a more barren time in the Motor City, as the Wings have failed to advance past the second round since 2009. But with 11 championships and a playoff streak of over 30 years, Detroit’s status as an iconic NHL franchise seems secure.
Boston Bruins
The Boston Bruins had to wait nearly 30 years for their first taste of Stanley Cup glory, as three trips to the final between 1929 and 1939 resulted in disappointment. But once the B’s broke through to win their first title in 1939, it opened the floodgates for nearly a decade of dominance.
Sparked by the legendary “Kraut Line” of Milt Schmidt, Woody Dumart and Bobby Bauer, along with rookie goaltending sensation Frank Brimsek, the Bruins beat the Toronto Maple Leafs in five games to claim the 1939 Cup. Improbably, Boston repeated the very next year, taking down the New York Rangers in a six-game final.
After falling short against Detroit in 1942, the Bruins authored their most memorable championship season in ’41. Led by the “Krauts” along with top defenseman Eddie Shore, Boston reeled off 11 straight playoff wins, including a four-game sweep of the Red Wings in the final. It stands as one of the NHL’s most dominant Cup runs.
The 1970s produced Boston’s most beloved team, affectionately known as the “Big Bad Bruins.” Anchored by superstars Bobby Orr, Phil Esposito, Johnny Bucyk and Gerry Cheevers, the B’s captured Cups in 1970 and 1972 in freewheeling fashion. The iconic image of Orr flying through the air after scoring the 1970 clinching goal remains one of hockey’s most memorable moments.
After several near misses in the late ’70s and ’80s, Boston claimed its last championship (to date) in 2011 behind Conn Smythe-winning goaltender Tim Thomas. With stars like Patrice Bergeron, Zdeno Chara, David Krejci, Brad Marchand and Tuukka Rask, the Bruins remain perennial contenders nearly a decade later.
Chicago Blackhawks
Although Chicago has six total Stanley Cup titles in its trophy case, they have all come within a concentrated window of just over 20 years. Prior to 2010, the Blackhawks possessed one of the longest championship droughts in NHL history.
One of the league’s charter members in 1926-27, Chicago reached its first Cup final in 1931. There they fell to the Montreal Canadiens, the first of many agonizing losses at the hands of the Habs. The Hawks had to wait over three decades just to get back to the last round, finally breaking through to defeat Detroit for the 1961 title.
Powered by Bobby Hull, Stan Mikita and longtime goalie Glenn Hall, the Blackhawks nearly established a dynasty in the 1960s. After winning it all in ’61, Chicago reached the final the following three seasons before losing each time to Montreal.
The Cup seemed destined to elude the Blackhawks after that, as decades of mediocrity followed. A generation of Chicago stars came and went without winning it all, including Hall of Famers like Denis Savard, Chris Chelios and Tony Esposito.
But the 21st century finally brought redemption for long-suffering Blackhawks fans. Built around Jonathan Toews, Patrick Kane, Duncan Keith and Brent Seabrook, Chicago ended its 49-year title drought by beating Philadelphia in six games in 2010. Incredibly, the Hawks followed up that breakthrough by winning it all again in 2013 and 2015 to become hockey’s latest dynasty.
Six championships may seem modest by Montreal’s lofty standards, but Blackhawks supporters now know the intoxicating feeling of prolonged success. And with a talented core still in place, more Cup parades could be coming to the Windy City before long.
The Winning Tradition of the Canadiens
As illustrated above, the Montreal Canadiens are in a Stanley Cup league of their own with 23 championships. The franchise has endured for over a century now, producing iconic moments and legendary players at every turn.
Names like Richard, Beliveau, Lafleur, Roy and the rest resonate as titans of hockey history. Meanwhile, the images of the dynastic 1970s Habs executing their fluid, mesmerizing attack are etched in the memories of fans.
Despite going nearly 30 years without a Cup, no team can match the Canadiens for winning tradition and prestige. Simply by donning the iconic red, white and blue uniform, Montreal players inherit the weight of expectations. It’s a responsibility to uphold the standards of a franchise that considers anything less than a championship a failure.
As the NHL’s most decorated team by far, the Canadiens are hockey royalty. While clubs like the Maple Leafs, Red Wings, Bruins and Blackhawks have carved out their own stories of success, Montreal remains the standard-bearer.
Recent Stanley Cup Trends
In looking at the bigger Stanley Cup picture beyond the teams with the most titles, some interesting trends emerge in the last 20-25 years:
- No team has repeated as champions since the Detroit Red Wings in 1997 and 1998. Parity has made it increasingly difficult to win back-to-back Cups in the salary cap era.
- Only one Canadian team has won the Cup since 1993 – the Montreal Canadiens in 1993. The majority of recent champions have been U.S. clubs like Pittsburgh, Chicago, Los Angeles and St. Louis.
- Nine different Western Conference teams have won the Cup in the past decade versus just three from the East (Pittsburgh twice, Washington and Boston). Teams from the West seem to have adapted better to the quicker, higher-skilled style of contemporary hockey.
- Having an elite goalie capable of getting hot at the right time seems essential to Cup success. Recent winning netminders include Jonathan Quick, Braden Holtby, Matt Murray and Jordan Binnington.
- Established superstars can still drive championship runs as proven by Sidney Crosby, Jonathan Toews, and Alexander Ovechkin in recent years.
So while dynasties appear harder to build under tightened NHL financial regulations, savvy management, opportune coaching and stellar goaltending at the right moments can all combine to produce magical Stanley Cup runs.
The Hunt for the Cup Continues
Winning Lord Stanley’s hallowed trophy remains hockey’s ultimate ambition. For clubs like the Toronto Maple Leafs enduring 50-plus years without a Cup, the desperation only grows as each season passes.
Even teams that have recently won like Chicago and Los Angeles face pressure to lift the Cup again before their championship core players age and decline. Windows of opportunity are fleeting.
In 2021-22, the Colorado Avalanche emerged as the NHL’s best regular season squad. Backstopped by elite netminder Darcy Kuemper, the Avs will look to translate that success into the franchise’s first title since 2001.
But the two-time defending champion Tampa Bay Lightning still loom as the team to beat until dethroned. Goaltender Andrei Vasilevskiy and playoff scoring machine Nikita Kucherov form a formidable championship pedigree.
Like any vigorous playoff run, winning it all comes down to grit, game-breaking skill and luck at the right moments. Even the NHL’s greatest dynasties needed those ingredients to cement their legacies. That’s what makes the Stanley Cup the most prized and cherished trophy in sports.
