For hockey fans and players, there’s no better feeling than winning the Stanley Cup. It’s a long, arduous journey from the first regular season game in October to the final game in June, especially after two pressure-packed months of playoffs. Sixteen teams make the postseason, but only one gets to lift Lord Stanley’s Cup.

No wonder so many teams have never done it. Of the NHL’s 32 franchises, 11 are still searching for their first title.

On the other hand, a handful of teams have dominated the Stanley Cup, winning numerous titles throughout the years with multiple dynasties. Playoff hockey can feel random sometimes (especially if you bet on it), but several teams keep finding ways to rise to the top.

With that in mind, here’s a look at which NHL teams have won the most Stanley Cups.

Teams With Most Stanley Cup Wins

The Montreal Canadiens have won the most Stanley Cups with 24, nearly twice as many as any other team. They are one of three teams with at least 10 championships.

Two Stanley Cup winners, the Montreal Maroons and St. Louis Eagles, are no longer active franchises. The Eagles won four Cups while the Maroons won two.

Additionally, the Stanley Cup was not played in 1919 due to the Spanish Flu and in 2005 due to the lockout.

Let’s look at the active NHL teams that have won at least two Stanley Cups.

Montreal Canadiens (24)

As mentioned, the Canadiens have won the most Stanley Cups in NHL history. Nobody else is close to them, as they’ve won 11 more titles than the second-place team.

The Habs won all of their championships during the 20th century, with their most recent coming in 1993. Montreal claimed at least one title in every decade from the 1910s to the 1990s.

The Canadiens were at their best from the 1950s to the 1970s, winning a whopping 16 titles in 27 seasons from 1953 to 1979 (including an NHL-record five consecutive championships from 1956 to 1960).

Fittingly, the Canadiens are the last Canadian team to win the Stanley Cup.

Toronto Maple Leafs (13)

The Maple Leafs are a distant second with 13 Stanley Cups, but that number is nothing to sneeze at.

Toronto won most of its titles during two separate dynasties. The first one came right after World War II, as the Maple Leafs won five titles in seven seasons from 1945 to 1951, including three straight from 1947 to 1949.

Toronto enjoyed another dynasty in the 1960s with four championships in six seasons from 1962 to 1967, including three straight from 1962 to 1964.

Unfortunately for the Maple Leafs, they haven’t won a title since 1967 – the longest active championship drought in the league.

Detroit Red Wings (11)

With 11 championships, Detroit has won the most Stanley Cups of any NHL team based in the United States.

The Red Wings enjoyed multiple periods of success during the league’s early years. They won back-to-back championships during the 1930s, two Stanley Cups during the 1940s and three straight titles in the 1950s. 

After that, Detroit endured several lean decades before returning to championship glory in the 1990s, winning three titles in a six-year period from 1997 to 2002. The franchise’s most recent Stanley Cup win was in 2008.

Boston Bruins (6)

Boston has won a lot of championships lately, so it’s not surprising to see the Bruins on this list.

Despite being one of the more successful franchises in NHL history, Boston has never had a dynasty. The Bruins won their first Cup in 1929, then won two more in 1939 and 1941.

The most famous era in franchise history was the “Big Bad Bruins” of the 1970s. Led by Hall of Fame defenseman Bobby Orr, Boston won a pair of titles in 1970 and 1972.

The Bruins’ sixth and most recent Stanley Cup came in 2011, ending a 39-year championship drought. 

Chicago Blackhawks (6)

The Blackhawks are tied with the Bruins for the fourth-most Stanley Cup wins, including the second-most for a U.S.-based franchise. 

Chicago enjoyed early success with two championships in the 1930s, but didn’t win again until 1961. 

After failing to win a title for nearly 50 years, the franchise finally turned things around under owner Rocky Wirtz in the late 2000s. The Blackhawks immediately became one of the best teams in the NHL, winning three Stanley Cups in a six-year span from 2010 to 2015.

Edmonton Oilers (5)

The Oilers didn’t join the NHL until 1979, but they’ve been one of the league’s most successful franchises over the last 45 years. Their five championships are tied with the Pittsburgh Penguins for the most in the league during that time.

All of Edmonton’s titles came during the 1980s. Led by Wayne Gretzky, the Oilers’ dynasty produced five Stanley Cups in seven seasons from 1984 to 1990 during one of the greatest runs in NHL history.

If Edmonton beats Florida in the 2024 Stanley Cup Finals, it will tie Boston and Chicago for the fourth-most championships in league history and become the first Canadian team since 1993 to win the Cup.

Pittsburgh Penguins (5)

Despite joining the league in 1967 as an expansion team, the Penguins have already won five Stanley Cups – tied with the Oilers for the most by a non-Original Six franchise.

Pittsburgh won back-to-back championships in 1991 and 1992. Led by Sidney Crosby, the Penguins won three Stanley Cups during a nine-year span from 2009 to 2017. 

With its 2016 and 2017 titles, Pittsburgh became the first NHL team to win consecutive championships in the salary cap era.

New York Islanders (4)

Founded in 1972, the Islanders enjoyed most of their success early on. They won all four of their Stanley Cups consecutively from 1980 to 1983, making them the last team in any major professional North American sport to win four straight championships. They’re also the last NHL team to win three consecutive Stanley Cups.

New York won 19 straight playoff series from 1980 to 1984 – a record in North American professional sports. Unfortunately, the team has endured decades of struggles since then and has been unable to recapture its past glory.

New York Rangers (4)

The Rangers were one of the best teams during the NHL’s formative years. They were the first U.S.-based franchise to win the Stanley Cup in 1928 (their second season) before winning additional championships in 1933 and 1940.

After that, New York went more than half a century before lifting the Cup again, enduring years of irrelevance. Led by Mark Messier, the Rangers finally ended their title drought in 1994.

Colorado Avalanche (3)

Originally the Quebec Nordiques, the Avalanche won all three of their titles after relocating to Denver in 1995.

The Avalanche won the Cup in their first season in Colorado, sweeping the Florida Panthers in the Stanley Cup Finals and becoming the first Denver-based team to win a professional sports title.

Colorado won another championship in 2001 and a third in 2022.

New Jersey Devils (3)

Founded in 1974, the Devils emerged as one of the NHL’s best teams around the start of the new millennium. Anchored by a strong defense, New Jersey won three Stanley Cups in a nine-year span, claiming titles in 1995, 2000 and 2003.

The Devils remained contenders throughout the 2000s but have struggled to find sustained success in the 2010s and 2020s.

Tampa Bay Lightning (3)

The Lightning were founded as an expansion franchise in 1992 and won their first Stanley Cup in 2004, but most of their success has occurred over the past decade.

Tampa Bay made four Stanley Cup Finals in eight seasons from 2015 to 2022, including three straight from 2020 to 2022. The Lightning won back-to-back championships in 2020 and 2021, making them the youngest and southern-most team with at least three titles.

Los Angeles Kings (2)

The Kings were founded as an expansion franchise in 1967. Despite having Wayne Gretzky for eight seasons and reaching the Stanley Cup Finals in 1993, they didn’t win their first championship until 2012.

Los Angeles didn’t wait long to win its second title, lifting the Cup again two years later in 2014 with a five-game win over the Rangers.

Philadelphia Flyers (2)

The Flyers were also part of the 1967 expansion and were the first expansion team of the post-Original Six era to win the Stanley Cup. Known as the “Broad Street Bullies,” Philadelphia won back-to-back championships in 1974 and 1975.

Despite making numerous postseason appearances and several deep playoff runs since then, the Flyers are still searching for their third title.