10 NHL Teams With the Most Stanley Cups

According to league records, the franchise only won four titles: 1920, 1921, 1923, and 1927. However, the franchise did win the Stanley Cup in 1903, 1904, 1905, 1906, 1909, 1910, and 1911. The Senators relocated to St. Louis in 1934, playing one season in the Midwest before folding operations in 1935.

9. New York Rangers (Four)

Championships: 1928, 1933, 1940, 1994

The New York Rangers joined the NHL in 1926 and lost in the Semi-Finals their first season before capturing the franchise’s first championship in 1928. They lost in the Final in 1929 and 1932 before winning again in 1933. New York only missed the playoffs once in their first 15 seasons, winning another Stanley Cup in 1940.

However, that would be their last victory for almost half a century before Mark Messier and the 1994 Rangers ended a 54-year drought, which was an NHL record at the time. During that stretch, the franchise lost in the Stanley Cup Final in 1950, 1972, and 1979. The Rangers’ most recent shot at a championship came in 2014 when they lost in five games to the Los Angeles Kings.

8. New York Islanders (Four)

Championships: 1980, 1981, 1982, 1983

As of 2024, the New York Islanders stand tall as the last true dynasty in the NHL, having not just won but dominated with four consecutive Stanley Cup titles from 1981 to 1983. Moreover, the Islanders are the last team to appear in the Final five straight times, losing their dynasty to the Edmonton Oilers in 1984. 

After joining the NHL in 1972, New York built up a lineup with future Hall of Famers like Denis Potvin, Mike Bossy, and Billy Smith. Together, these kids became adults and awarded the Long Island fans four championships within 10 years of inception. Unfortunately, the Islanders haven’t returned to the Stanley Cup Final in the past 40 seasons.

7. Pittsburgh Penguins (Five)

Championships: 1991, 1992, 2009, 2016, 2017

The Pittsburgh Penguins, a team that joined the NHL in 1967 and initially struggled, experienced a remarkable turnaround after drafting Mario Lemieux in 1984. This marked a new era for the franchise, leading to back-to-back Stanley Cup titles in 1991 and 1992. Of course, Lemieux’s exceptional performance earned him the Conn Smythe both times, a team record eventually tied by Sidney Crosby in 2016 and 2017.

Although Pittsburgh didn’t return to the Stanley Cup Final until 2008, they won their third championship in 2009 and another back-to-back in 2016 and 2017. As owner of the Penguins during their past three title wins, Lemieux is the only person associated with the organization to have his name on the Stanley Cup five times.

6. Edmonton Oilers (Five)

Championships: 1984, 1985, 1987, 1988, 1990

The Edmonton Oilers dominated in the 1980s, not because Wayne Gretzky scored 1,669 points in his first eight seasons, but because the organization was just two seasons removed from winning seven consecutive Stanley Cup titles. After dethroning the four-time champion Islanders in 1984, they won again in 1985 before missing the Final in 1986.

In 1987, the Oilers returned to the top of the NHL mountain, winning again in 1988, Gretzky’s last season in Edmonton. Then, under new leadership, Messier led the organization to their most recent Stanley Cup title in 1990. Since their last triumph, the Oilers returned to the Final in 2006, losing in seven games to the Carolina Hurricanes.

5. Boston Bruins (Six)

Championships: 1929, 1939, 1940, 1970, 1972, 2011

The Boston Bruins are one of many Original Six franchises that experienced a lengthy championship drought, going 39 years between Stanley Cup titles. Since their inception in 1926, the Bruins have appeared in the Stanley Cup Final 20 times, almost equal to the number of times the organization has missed the playoffs in 100 seasons, 22 times.

Despite not holding the record for most Stanley Cup titles, Boston has a record that no team may break in our lifetime: qualifying for the playoffs for 29 straight seasons from 1967 to 1996. During this streak, the Bruins won two titles in 1970 and 1972 while playing in the Stanley Cup Final in 1974, 1977, 1978, 1988, and 1990.

The club also won the league championship in 1929, 1939, and 1940. Even though their most recent victory came in 2011, the Bruins will always be associated with the Stanley Cup. Bobby Orr scored the most iconic goal in NHL history, flying through the air after the Cup-clinching goal in 1970.

4. Chicago Blackhawks (Six)

Championships: 1934, 1938, 1961, 2010, 2013, 2015

The Chicago Blackhawks were very successful in the early days, winning the Stanley Cup twice within 12 years of forming in 1926. After losing in the Final in 1931, they rebounded to capture the championship in 1934 and 1938. Unfortunately, the franchise went into a dark period, only qualifying for the playoffs three times between 1943 and 1958.

However, the Blackhawks turned a page in the early 1960s, thanks to Hall of Famers Stan Mikita and Bobby Hull, who ended the championship drought in 1961. Between 1959 and 1997, Chicago missed the playoffs just once and played in the Stanley Cup Final five times in 1962, 1965, 1971, 1973, and 1992. After 49 years, Jonathan Toews and Patrick Kane ushered in a new era of Blackhawks hockey, winning three titles in 2010, 2013, and 2015. 

3. Detroit Red Wings (11)

Championships: 1936, 1937, 1943, 1950, 1952, 1954, 1955, 1997, 1998, 2002, 2008

The Detroit Cougars joined the NHL in 1926 and became the iconic Red Wings in 1933. From 1936 to 1955, the organization won seven Stanley Cup titles, including two back-to-back sets in 1936 and 1937, followed by 1954 and 1955. In between, they won titles in 1943, 1950, and 1952. As one of the most successful franchises, Detroit has been home to Hall of Famers like Marty Barry, Herbie Lewis, Ebbie Goodfellow, Gordie Howe, Alex Delvecchio, and Terry Sawchuk, all instrumental players in those first championships.

Like other Original Six franchises, the Red Wings entered a dark era from 1967 to 1983, qualifying for the playoffs just twice. But the good times were right around the corner. Through the draft, Detroit selected players like Steve Yzerman, Nicklas Lidström, Pavel Datsyuk, and Henrik Zetterberg, who helped the franchise play in the postseason from 1991 to 2016, winning the Stanley Cup in 1997, 1998, 2002, and 2008. 

2. Toronto Maple Leafs (13)

Championships: 1918, 1922, 1932, 1942, 1945, 1947, 1948, 1949, 1951, 1962, 1963, 1964, 1967

The Toronto Maple Leafs have won the second-most Stanley Cup titles in NHL history. However, they are the last team to win a championship in the Original Six era, which ended in 1967. That distinction gives them the longest title drought of all time. Moreover, the organization has not appeared in the Final since the league expanded from six to 12 teams almost six decades ago.

However, it hasn’t all been doom and gloom, as the Toronto Arenas won the first-ever NHL Stanley Cup title in 1917-18. Then, as the St. Patricks, they won another title in 1922 before switching their branding to the Maple Leafs in 1927. Within five seasons, the organization celebrated its third championship (1932) while playing in the Final six times between 1933 and 1941, capturing another title in 1942.

With their fifth Stanley Cup win in 1945, the Maple Leafs would three-peat from 1947 to 1949 and add another title to the mantle in 1951. After a decade with no championships, the Maple Leafs would win four in six years, including another three from 1962 to 1965, with that exclusive final title in 1967. 

1. Montreal Canadiens (24)

Championships: 1916, 1924, 1930, 1931, 1944, 1946, 1953, 1956, 1957, 1958, 1959, 1960, 1965, 1966, 1968, 1969, 1971, 1973, 1976, 1977, 1978, 1979, 1986, 1993

The Montreal Canadiens are the most successful team in NHL history, having won the coveted Stanley Cup a record 24 times. Their championship total is only second to the New York Yankees (27) for the most by a franchise in the four North American sports leagues. Walking into the Bell Centre to see all the Stanley Cup banners hanging in the rafters is a testament to the Canadiens’ unheralded success in 106 seasons.

As of 2024, Montreal remains the last Canadian team to win the Stanley Cup. It achieved this feat in 1993 when Patrick Roy led the team to their 24th championship, capturing the Conn Smythe Trophy for the second time, duplicating his feat from 1986. Since winning four in a row from 1976 to 1979, the Canadiens have only played in the Final three times, winning two, the least number of championships during any 40-year stretch in franchise history.

Founded in 1909, the Canadiens won the Stanley Cup for the first time in 1915-16, an accomplishment the franchise recognizes but the NHL does not. According to league records, they are 23-time champions. During their first NHL season, they lost in the Final before winning it in their second season in 1918-19. After missing out on the playoffs, they were finalists from 1923 to 1925, winning back-to-back in 1924 and 1925. 

In 1931 and 1932, they won their second set of back-to-back titles before winning in 1944 and 1946, giving them seven Stanley Cup titles in their first 30 seasons. However, this was only the beginning of something special. After losing in the 1947 Final, Montreal missed the playoffs in 1948 before embarking on their first great run. Starting in 1951, the Canadiens skated in the Stanley Cup Final for the next 10 seasons, winning in 1953 and becoming the first and only team in NHL history to win five consecutive championships from 1956 to 1960. 

From 1961 to 1964, the Canadiens didn’t advance past the Semi-Finals but won back-to-back titles in 1965 and 1966, lost in the Final in 1967, and finished the decade with titles in 1968 and 1969. Their 20-year consecutive playoff streak ended in 1970, but Montreal would win two of the following three Stanley Cups in 1971 and 1973 before closing out the 1970s with four titles from 1976 to 1979.

Since joining the NHL in 1917, Montreal missed the playoffs just nine times in its first 80 seasons. On top of holding the record for most Stanley Cup titles, the Canadiens have played in the Stanley Cup Final 34 times. Some of the game’s greatest players have their names on the Silver Chalice a record number of times, like Henri Richard, who won 11 titles as a player. In contrast, Jean Beliveau is etched into history 17 times, winning 10 as a player and seven as a team executive.

Overall, the Canadiens hold numerous records regarding the Stanley Cup, and there are many milestones that no team will ever challenge or break. Considering how much parity there is in the NHL today, just like the Yankees in the MLB, Montreal can consider itself the most successful franchise of all time, with its place in history safely secured.