Which are the best and most winningest franchises in NHL history? Bonus: which are the most valuable?

In the world of hockey, certain franchises have established themselves as powerhouses, leaving a lasting impact on the sport. This article will rank the most successful NHL franchises, exploring their achievements, legendary players, and pivotal moments that have defined their legacies. Understanding these franchises can provide valuable insights for fans and fantasy hockey players alike!

The Best NHL and Hockey Franchises of all time

The NHL is built upon franchise success. The ability of teams to sustain success over a lengthy period helps build the fanbase and interest in the franchise.

We’ll be taking a look at some of the best NHL franchises of all time throughout this article with Stanley Cups, regular season success and more.

Top 10 Most Successful NHL Franchises of All Time

10. Philadelphia Flyers - 2 Stanley Cups

The Philadelphia Flyers came into the league in the expansion of 1967 and found success relatively quickly. They’ve only won the Stanley Cup two times in their history and both came in their first 10 years of existence in 1974 and 1975, but they've maintained a legacy of success and influence with their more than 40 playoff appearances.

Bobby Clarke set the tone for the Broad Street Bullies in the 1970s with goaltender Bernie Parent between the pipes. They’ve since had legends like Mark Howe, Eric Lindros, Ron Hextall, and more recently Claude Giroux wear the Orange and Black.

9. Colorado Avalanche - 2 Stanley Cups

The Quebec Nordiques came into the league in the 1970s but moved to Denver to become the Colorado Avalanche in 1995. The Avs proceeded to win the Stanley Cup in their inaugural season and then again in 2001 and 2022.

Legends Joe Sakic, Peter Forsberg, and Patrick Roy were on that first Stanley Cup team with Milan Hejduk, Adam Foote and Ray Bourque joining as well.

8. Edmonton Oilers - 5 Stanley Cups

The Edmonton Oilers have had a few of the greatest players of all time in Wayne Gretzky and Connor McDavid. Gretzky helped lead an Oilers dynasty in the 1980s after the franchise joined the NHL in 1979.

The Oilers’ five Stanley Cup victories all came in a seven-year span in 1984, 1985, 1987, 1988 and 1990. They reached the Stanley Cup Final in 2024 but lost in heartbreaking fashion in game seven.

7. Pittsburgh Penguins - 6 Stanley Cups

The Pittsburgh Penguins have had a few different eras with a pair of legends leading the way. First it was Mario Lemieux and Jaromir Jagr in the 1990s before Sidney Crosby and Evgeni Malkin took the reins in the 2000s.

The Pens won back-to-back Stanley Cups in 1991 and 1992 and then again in 2016 and 2017 with a 2009 victory in the middle.

6. Boston Bruins - 6 Stanley Cups

The Boston Bruins are an Original Six team and have been one of the classic franchises in NHL history. They’ve won the second-most games in NHL history with over 3,400 and have six Stanley Cups to show for it.

The B’s won three Stanley Cups in the early days of the NHL (1929, 1939, 1941), two more in the 1970s, and most recently in 2011.

Ray Bourque, Johnny Bucyk, Patrice Bergeron and Phil Esposito are some of the franchise’s all-time greats.

5. Chicago Blackhawks - 6 Stanley Cups

The Chicago Blackhawks are another Original Six team that have had success in a few different eras. They won two Stanley Cups in the 1930s (1934 and 38), then in 1961 before a long drought until 2010.

Jonathan Toews and Patrick Kane led the way for the 2010s dynasty that won the Stanley Cup in 2010, 2013, and 2015. Other legendary Blackhawks include Stan Mikita, Bobby Hull and Denis Savard.

4. New York Islanders - 4 Stanley Cups

In comparison to many of the other teams in the Top 10, the New York Islanders have a smaller number of Stanley Cups won in franchise history (four), but they were one of the most dominant teams in NHL history during those four seasons.

The Islanders won four straight Stanley Cups to start the 1980s after reaching the Stanley Cup Finals in 1978 and 1979. Bryan Trottier, Mike Bossy and Denis Potvin are the top scorers in Islanders history.

3. Toronto Maple Leafs - 13 Stanley Cups

The Leafs started in the NHL in 1917 (originally as the Toronto Arenas) and have been one of the league's most storied and decorated franchises ever since, tied for second most NHL championships among all teams. But while the Maple Leafs were a dominating franchise for the first 50 years, the team is now known for its exceedingly long title drought, having not won a Stanley Cup since 1967.

The Leafs have seen legends like Mats Sundin, Dave Keon, Darryl Sittler, Johnny Bower, Tim Horton and Doug Gilmour suit up throughout their 100-plus-year history.

2. Detroit Red Wings - 11 Stanley Cups

The Detroit Red Wings are another Original Six team that has found success throughout its history. Their 11 Stanley Cup victories are the most by a team based in the United States. Their first seven came before expansion (1936, 1937, 1943, 1950, 1952, 1954, 1955) and they had to wait over 40 years for their next one.

Steve Yzerman helped the Red Wings to back-to-back Stanley Cups in 1997 and 1998 with the franchise winning two more in 2002 and 2008.

Gordie Howe is one of the best NHL players of all-time and played 1,687 games with the Red Wings. Alex Delvecchio and Nicklas Lidstrom are among the list of other Detroit legends.

1. Montreal Canadiens - 24 Stanley Cups

The Montreal Canadiens may not have had much success in recent memory but they can always point to their mind-boggling 24 Stanley Cup victories in franchise history. They’re also the only NHL franchise to win over 3,500 regular-season games.

The Canadiens were the class of the NHL in the early days as they won multiple Stanley Cups in the ‘30s, ‘40s, ‘50s, ‘60s, ‘70s, and ‘80s.

Unfortunately, the Canadiens' most recent Stanley Cup win came way back in 1993. That’s still the most recent win by any Canadian franchise.

Guy Lafleur, Jean Beliveau and Henri Richard lead the franchise in all-time points.

NHL Franchise Valuations

There are a few different factors when it comes to an NHL franchise’s valuation. Market size is a key one as are TV ratings, fan engagement/attendance and historic performance.

The top-valued NHL franchises as of 2025 are the Toronto Maple Leafs, New York Rangers, Montreal Canadiens, Los Angeles Kings, and Boston Bruins.

Importance of NHL Franchise Success for Fantasy Hockey

It’s important to understand which NHL franchises have a history of success for fantasy hockey. The more historically successful programs may invest more heavily in putting a winning team on the ice. While there are always up-and-coming franchises as well, teams with long track records of success often feel significant pressure from their fanbases to get back to the top.

Frequently Asked Questions

The most popular NHL franchises include the Chicago Blackhawks, Boston Bruins, and Pittsburgh Penguins.

What is the most winning franchise in the NHL?

The Montreal Canadiens are the winningest franchise in NHL history both in terms of regular-season wins (3,500+) and Stanley Cup victories (24).

What NHL team has the best start?

The Vegas Golden Knights made the Stanley Cup Final in their inaugural season in 2017-18.

Which franchise has won the most Stanley Cups?

The Montreal Canadiens have won the most Stanley Cups with 24.

How do these franchise rankings affect player performance in fantasy hockey?

They don't have any impact on player quality. However, the most successful franchises historically speaking tend to chase after the best players.

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