Who has won the most Stanley Cup championships?

The Stanley Cup is the championship trophy awarded annually to the National Hockey League (NHL) playoff winner. It is the oldest professional sports trophy in North America and is surrounded by decades of history and lore as the most coveted prize in hockey.

Quick Facts

Here are some key facts about Stanley Cup wins:

  • The Montreal Canadiens have won the Stanley Cup 24 times, the most of any NHL team.
  • The Toronto Maple Leafs have won 13 Stanley Cups, second only to Montreal.
  • The Detroit Red Wings have 11 Stanley Cup wins while the Boston Bruins have 6.
  • The Pittsburgh Penguins and Edmonton Oilers are tied for the most Cups among non-Original Six teams with 5 each.
  • Among active NHL franchises, the team with the longest Stanley Cup drought is the Toronto Maple Leafs, who last won in 1967.

History of the Stanley Cup

The Stanley Cup was first awarded back in 1893 as the championship trophy for Canada’s top amateur hockey club. It was donated by Sir Frederick Arthur Stanley, Lord Stanley of Preston and son of the Earl of Derby, who wanted to recognize the top hockey team in Canada. After Lord Stanley retired as Governor General, the first Stanley Cup playoff took place in 1894 between the Montreal Amateur Athletic Association (MAAA) and the Ottawa Capitals, with the MAAA claiming the first Cup victory. The trophy was then awarded to amateur teams exclusively until 1910 when it became the championship trophy of the NHL.

The NHL competed against the Western Canada Hockey League (WCHL) and the Pacific Coast Hockey Association (PCHA) for the Cup until 1926 when the three leagues merged under the NHL banner. Since 1926-27 season, the Stanley Cup has been exclusively awarded to the playoff champion of the NHL.

The trophy itself has changed over the years as bands have been added to engrave the names of each year’s winning team members. The original bowl of the cup was retired in 1969 as it had grown too brittle and fragile from years of engraving. It was replaced with a replica which is currently still used.

Stanley Cup Traditions

Lifting the Stanley Cup to celebrate the championship victory is one of hockey’s most revered traditions. Each winning team member gets to spend a day with the Cup during the off-season, a tradition that started in 1995. The Cup has traveled worldwide with NHL players, even visiting Afghanistan with Washington Capitals’ Alex Ovechkin.

Another unique tradition is that each team member, from players to staff, gets to drink champagne from the bowl of the Cup on ice after clinching the championship. This has led to plenty of amusing photos over the years.

All-Time Stanley Cup Championships by Team

Here is the complete list of NHL franchises ranked by number of Stanley Cup wins:

Team Number of Stanley Cup Wins Most Recent Win
Montreal Canadiens 24 1993
Toronto Maple Leafs 13 1967
Detroit Red Wings 11 2008
Boston Bruins 6 2011
Chicago Blackhawks 6 2015
Edmonton Oilers 5 1990
Pittsburgh Penguins 5 2017
New York Islanders 4 1983
New York Rangers 4 1994
New Jersey Devils 3 2003
Colorado Avalanche 2 2001
Los Angeles Kings 2 2014
Philadelphia Flyers 2 1975
Tampa Bay Lightning 2 2020
Anaheim Ducks 1 2007
Calgary Flames 1 1989
Carolina Hurricanes 1 2006
Dallas Stars 1 1999
Ottawa Senators* 1 1927
St. Louis Blues 1 2019
Washington Capitals 1 2018

*The original Ottawa Senators franchise, not the current franchise with the same name.

As the table shows, the Montreal Canadiens are far and away the leader with 24 Cup wins between 1916 and 1993. The Toronto Maple Leafs rank second with 13 Cup victories but have not won since 1967, leaving them with the longest active drought in the NHL.

Montreal Canadiens Dominance

The Montreal Canadiens dominated in the early years of the NHL, winning 6 Stanley Cups between 1916 and 1925. This included a 4-year stretch where they won the Cup every season from 1956 to 1960.

The Canadiens had a particularly impressive run in the 1970s, winning 6 championships in the decade. This included 4 straight Stanley Cup titles from 1976 to 1979, a feat no other team has matched since the NHL expanded beyond the Original Six franchises.

Stars like Maurice “Rocket” Richard, Jean Beliveau, and Ken Dryden were key contributors across Montreal’s championship runs over the decades. Goaltender Patrick Roy powered their last two Cup wins in 1986 and 1993.

Since 1993, however, the Canadiens have yet to return to another Stanley Cup Final. Their 24-year drought is one of the longest in their history, despite having superstar goaltender Carey Price, though they did make an unexpected run to the 2021 Cup Final before ultimately falling to the Tampa Bay Lightning.

Other Notable Team Dynasties

While no team has dominated like the Canadiens, here are some other memorable championship runs in NHL history:

  • New York Islanders (1980 – 1983): The Islanders won 4 straight Cups in the early 1980s, led by forwards Bryan Trottier and Mike Bossy along with their stingy defense and goaltending.
  • Edmonton Oilers (1984 – 1990): The Wayne Gretzky-led Oilers won 5 Cups in 7 seasons, including their 1988 title after Gretzsky was infamously traded to the L.A. Kings.
  • Pittsburgh Penguins (1991 – 1992, 2016 – 2017): Mario Lemieux captained back-to-back Cup wins in the early 90s. Sidney Crosby and Evgeni Malkin led their more recent repeat efforts decades later.
  • Detroit Red Wings (1997 – 1998, 2002, 2008): Goalie Dominik Hasek was a key part of Detroit’s late 1990s mini-dynasty. Nicklas Lidstrom and Pavel Datsyuk were stalwarts in their 2000s championship teams.

Stanley Cup Playoff Format

Winning the grueling two month marathon that is the NHL’s Stanley Cup Playoffs is a formidable challenge. The playoff format to determine the Stanley Cup champion has undergone many changes over the decades.

Today, 16 teams qualify for the playoffs – 8 from each conference. The top 3 teams from each of the 4 divisions make it along with 2 wild card teams from each conference.

The first two rounds are intra-conference matchups, with the top seed playing the wild card and the 2nd and 3rd place teams facing each other. The Conference Finals pit the two remaining teams in each conference against each other. Finally, the Stanley Cup Finals feature the Western Conference playoff champion versus the Eastern Conference champion.

All series are best-of-seven, with the first team to win four games advancing to the next round. The higher seed has home-ice advantage and hosts Games 1, 2, 5, and 7 while the lower seed hosts Games 3 and 4. This 2-2-1-1-1 format has been used since 2014.

Playoff Seeding Criticisms

There has been criticism over teams in weaker divisions potentially getting higher seeds. Division winners are guaranteed a top 3 seed even if a non-division winner has a better record. In theory, a team could win a poor division with a marginal record yet secure home ice over a wildcard team with a much better record.

However, some defend the system as it intensifies division rivalries as teams fight tooth and nail to secure those coveted automatic playoff spots. Ultimately, the consensus is that if the league emphasized overall record rather than division standings, it would ensure the highest quality matchups in later playoff rounds.

Notable Playoff Moments

The Stanley Cup Playoffs produce some of hockey’s most memorable moments. Here are some all-time greats:

Bobby Orr’s Stanley Cup Winning Goal

An iconic photo in NHL history is Bobby Orr’s Cup winning goal for the Boston Bruins in 1970. Orr flying through the air after scoring in overtime of Game 4 against the St. Louis Blues is one of hockey’s most famous images.

Mario Lemieux’s Goal Against the North Stars

Mario Lemieux displayed his sublime skill in the 1991 Finals against Minnesota. In Game 2, he split the defense and made a dazzling move to his backhand, showcasing his otherworldly talent.

Doug Gilmour Double Overtime Winner

In 1993, Doug Gilmour scored an electrifying goal for Toronto in the second overtime against St. Louis in Game 1, after taking a big hit moments earlier. The Maple Leafs would win the series, but fell short in the Conference Finals.

Matteau! Matteau! Matteau!

This call by Rangers broadcaster Howie Rose after Stephane Matteau’s overtime winner in Game 7 of the 1994 Eastern Conference Finals vs. New Jersey is etched in hockey lore. It ended the Rangers’ curse, propelling them to the Cup.

Recent Stanley Cup Trends

In the salary cap era starting after the 2004-05 lockout season, the Stanley Cup has been awarded to 10 different franchises. parody has increased across the league due to more evenly distributed talent.

No team has won back-to-back Cups since the Pittsburgh Penguins in 2016 and 2017. The last team to three-peat were the New York Islanders from 1980 to 1983.

Goaltending and depth scoring have been crucial in recent Stanley Cup runs. Teams need a hot goalie and balanced scoring across all four forward lines to weather the grind of the playoffs.

Prominence of American Teams

While Canadian teams dominated the Cup’s early history, American franchises have become increasingly prominent since the 1990s expansion into non-traditional hockey markets.

The New York Rangers’ triumph in 1994 was monumental for the league’s growth in the United States. Since then, teams like Colorado, Dallas, Carolina, Tampa Bay, and Anaheim have all celebrated Cup wins.

No Canadian team has hoisted the Cup since Montreal in 1993, with Vancouver, Calgary, Edmonton, and Ottawa coming agonizingly close in recent decades before ultimately falling short.

Conclusion

The Stanley Cup is one of the most revered trophies across all professional sports. Players give everything they have for the chance to hoist that sacred Cup over their heads and take their place in hockey immortality. While the Montreal Canadiens have far and away won the most titles, the Cup’s storied history is filled with memorable heroes and iconic moments from teams across the NHL.

Recent years have seen more parity across the league, with the Cup being won by different teams without much back-to-back success. Winning the marathon that is the NHL playoffs proves more difficult than ever. It will be fascinating to see which team is the next to etch their names on the Stanley Cup!

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