Every spring, 16 teams take to the ice to compete for the most beautiful trophy in sports. Even non-hockey fans have argued that the Stanley Cup is the best trophy. You can raise it high, you can drink from it, and you get your name engraved on it. No other trophy has that feature. As the NHL has expanded to 30 teams, it gets harder and harder for teams to rack up Stanley Cup victories, as the original six still occupy most of the Stanley Cup victories in history.
In recent years, we’ve actually seen a shift back to original six cup winners. Four of the last six cup winners are original six teams, Detroit in 2008, Boston in 2011 and Chicago in 2010 and 2013. There are teams with long cup droughts and teams still in search of their first championship.
The Stanley Cup was actually around before the NHL was formed, in 1917, with the first winner being the Montreal Hockey Club, affiliated with the Montreal Amateur Athletic Association (MAAA) in 1894. Amateur teams competed for the cup for 23 years before the cup went to the NHL. Without any further ado, here are the 11 teams with the most Stanley Cups in their history. We’ll rank the winners based on the NHL’s history, but be sure to point out the teams’ victories prior to the inception of the league.
11) New Jersey Devils — 3 Stanley Cups
The New Jersey Devils were once referred to as a Mickey Mouse team by the Great One, Wayne Gretzky back in the 1980s. The original franchise was founded in 1972 as the Kansas City Scouts, Colorado Rockies and finally the New Jersey Devils in 1982.
It was a tough road for the Devils, but they finally enjoyed a winning season in 1987-88. The arrival of rookie Martin Brodeur allowed them to force the Rangers to Game 7 overtime in the Eastern Conference Final in 1994.
The following year, coach Jacques Lemaire took them to the promised land, and set the Devils up as one of the more successful franchises of the past 20 years. Scott Stevens, Scott Niedermayer, Ken Daneyko, Stephane Richer, John McLean, Bobby Holik, Jason Arnott, Patrick Elias, Brian Gionta; all great Devils in the team’s history.
Their first cup came in 1995 with a win over the Detroit Red Wings. Five years later they took it home again, with Arnott’s cup-winning goal coming in overtime of Game 6 over Dallas.
In 2003, they ended the Mighty Ducks’ Cinderella season with a seven-game series win. In the past 20 years, the Devils have won three cups and have made five finals appearances.
10) Pittsburgh Penguins — 3 Stanley Cups
It took the Pittsburgh Penguins 24 years to win their first Stanley Cup. As part of the NHL’s original expansion in 1967, the Penguins had many lean years before they got the break they needed; the right to draft Mario Lemieux in 1984. They slowly built a championship team, trading for Paul Coffey, Tom Barrasso and bringing in Kevin Stevens, Rob Brown and John Cullen. Along came Ron Francis, Ulf Samuelsson, Larry Murphy. Finally they got Jaromir Jagr and the championship team was complete.
They won their first championship in 1991, edging out the Minnesota North Stars in six games. They followed that up by sweeping the Chicago Blackhawks for a second cup in 1992. Many expected them to build a dynasty but they wound up losing in seven games to the Islanders in the 1993 Patrick Division Final.
They came close, but the group never made it back to the Stanley Cup final. The Penguins eventually went through rough years as their legends grew older, but eventually got to draft Marc-Andre Fleury, Evgeni Malkin, Sidney Crosby and Jordan Staal to build a winner.
In 2009 they took home their third Stanley Cup and the team is in position to contend for the foreseeable future.
9) * Ottawa Senators — 4 Stanley Cups (+7 pre-NHL)
The current incarnation of the Ottawa Senators are still searching for their first Stanley Cup, but the original Senators were actually perhaps the most dominant team in the cup’s early years.
Their ‘Silver Seven’ era refers to their seven Stanley Cups won between 1903 and 1911. Seven cups in nine years!
After the NHL formed, the Senators again had a dominant run, this time with the ‘Super Six’ era, winning an additional four Stanley Cups between 1920 and 1927. Quite a rich history in a brief period of time. However, currently living Ottawa fans are still waiting to see one with their own eyes.
8) New York Islanders — 4 Stanley Cups
The New York Islanders have the most impressive dynasty after the Canadiens. They are the only other team to win four straight Stanley Cups, winning from 1980 to 1983.
Fans on Long Island are still longing (no pun intended) for these days, as inept management and unstable ownership have crippled the franchise.
Still, this run in the early 1980s was quite impressive. The team had Mike Bossy, Bryan Trottier, Denis Potvin, Bob Nystrom, Butch Goring and Clark Gilles.
Bob Nystrom’s cup-winning overtime goal in 1980 kicked off the dynasty. They then beat the North Stars and Canucks and knocked off the new kids, the Edmonton Oilers in 1983.
Their dynasty ended in 1984, losing in the final to those same Oilers. They nearly won five in a row. The team remained competitive, but the franchise has never gotten anywhere close to where they once were.
7) New York Rangers — 4 Stanley Cups
The Rangers have the least amount of cup wins amongst the original six, thanks to a 54-year cup drought between 1940 and 1994.
Their cups in 1928, 1933 and 1940 were long forgotten, as the team simply couldn’t keep up with their fellow original six teams.
By the time the 1980s came around, the chant of ‘1940’ was popular when the Rangers would visit opposing arenas in the playoffs.
In the early 1990s the Rangers were set on a mission to build a cup winner, essentially taking the pieces from Edmonton’s dynasty of the late 80s. They acquired Mark Messier, Glenn Anderson, Adam Graves, Craig MacTavish, Essa Tikkanen, Kevin Lowe and Jeff Beukeboom.
That went along with homegrown Rangers Mike Richter, Alexei Kovalev, Brian Leetch and Sergei Zubov.
It’s no surprise with that group that the Rangers took the cup, but it wasn’t easy. They needed a double overtime goal in Game 7 against New Jersey from Stephane Matteau and a 3-2 victory in Game 7 over the Vancouver Canucks.
The Rangers have made the playoffs many times in the last 20 years, reaching the conference finals in 1997 and 2012, but are still looking for their fifth cup.
6) Edmonton Oilers — 5 Stanley Cups
When you think of hockey in the 1980s, you think of the Edmonton Oilers. Fast-paced, run n’ gun, high-scoring, exciting hockey.
With a team containing Wayne Gretzky, Mark Messier, Paul Coffey, Jari Kurri, Glenn Anderson, Grant Fuhr, etc… you better win some cups. They won four in five years; 1984, 1985, 1987 and 1988.
The team made ‘the trade’ dealing Gretzky to Los Angeles in 1988, but managed to win it all without the Great One in 1990.
The Oilers soon lost all their stars of the decade, and have never been able to recover. The franchise was average after 1990 and after a surprise run to the final in 2006, they have not made the playoffs since.
Still, five cups in a relatively short history is impressive, the most for any non-original six team.
5) Chicago Blackhawks — 5 Stanley Cups
The Blackhawks fan base has finally been rewarded for their years of patience, with two cups in the last four seasons.
Prior to that, Chicago’s last cup had come in 1961. A 49-year dry spell until 2010.
The Blackhawks took home the cup in 1934 and 1938, but fell behind in the 40s and 50s. In 1961, they ended the Canadiens’ dynasty with an upset win in the semifinals and got by the Red Wings in the final. Bobby Hull, Al Arbour and Glenn Hall were some notable Hawks on the team.
The Bill Wirtz ownership years were brutal for Chicago fans, as Wirtz earned the name “Dollar” Bill for his frugality and stubbornness. He forbade home games to be televised locally. For a brief period, watching Hawks home games locally only happened if they made the playoffs, or fans had to order Hawkvision, a pay-per-view channel costing $29.95 a month.
Smart drafting and key signings finally brought the franchise back to life. Jonathan Toews, Patrick Kane, Duncan Keith and Brent Seabrook remain part of the core, while players like Marian Hossa, Patrick Sharp and others were savvy pickups. Probably the best managed team in the NHL and they could creep higher on this list in the near future.
4) Boston Bruins — 6 Stanley Cups
A 39-year slump was erased in 2011, when the Boston Bruins won their sixth Stanley Cup. Many in that group are still together and look very promising to eventually deliver more for Boston.
The franchise has typically gone through hot and cold periods in their history. They won cups in 1929, 1939 and 1941, before 29 years separated them from their next cup win in 1970.
Bobby Orr and Phil Esposito on the same team brought the Bruins cup wins in 1970 and 1972. The team would come close in the next 39 years multiple times, losing in the final in 1977, 1978, 1988 and 1990. The era of Ray Bourque and Cam Neely was spectacular, but there were no cup wins to show for it.
In 2011, their seven-game series win over Vancouver brought the cup back to Beantown and they gave the Blackhawks a scare in last year’s finals.
The team is definitely now set up for more success.
3) Detroit Red Wings — 11 Stanley Cups
The Detroit Red Wings have been the most consistent franchise in recent memory, with 23 straight playoff appearances, but this franchise had many tough years before they ended a 42-year drought in 1997.
They won cups in 1936, 1937 and 1943, but it was the arrival of Gordie Howe that allowed them to dominate the early 1950s.
Howe, along with Ted Lindsay and Sid Abel, formed the “Production Line” and helped the Wings to cup wins in 1950, 1952, 1954 and 1955.
After the “Dead Wings” era, Detroit came on strong in the 90s, building a team comprised of Steve Yzerman, Sergei Federov, Slava Fetisov, Igor Larionov, and Mike Vernon.
Led by Scotty Bowman, the Wings were upset in 1994 by the Sharks, in the 1995 final by the Devils and their 62-win season was all for naught in 1996 with a conference final loss to Colorado.
They added Brendan Shanahan and Larry Murphy in 1996-97 and went on to avenge their loss to Colorado and swept the Flyers in the 1997 final. They repeated by sweeping the Washington Capitals in 1998.
Remaining a contender, they once again got to the top of the mountain in 2002, adding Dominik Hasek, Luc Robitaille and Brett Hull and winning their third cup in six seasons.
A new core brought them the cup in 2008 with Nicklas Lidstrom, a key piece in the previous cup wins now leading the way, with Henrik Zetterberg, Johan Franzen, Pavel Datsyuk and others leading the way.
The Red Wings are in the midst of a youth movement, but remain competitive and always seem to be a threat in the playoffs.
2) Toronto Maple Leafs — 13 Stanley Cups
There it is; a picture of a cup-winning Maple Leafs team.
Including their cup wins under the names, the Toronto Pats and Toronto Arenas, the franchise has 13 Stanley Cups. The Conn Smythe era remains Toronto’s best.
The team won cups in 1918, 1922, 1932, 1942, 1945, 1947, 1948, 1949, 1951, and under new majority ownership in 1962, 1963, 1964 and finally 1967.
After many rough years, the Maple Leafs seemed poised to regain the cup in the 90s but final losses to Los Angeles and Vancouver ended those dreams.
The era of the late 90s and early 2000s saw them come close again, losing to Buffalo in the 1999 Eastern Conference Final, and to Carolina in 2002s conference final. Those teams were led by Pat Quinn and had the likes of Mats Sundin, Darcy Tucker, Alexander Mogilny, Gary Roberts, Brian McCabe, Curtis Joseph, Tomas Kaberle and Tie Domi.
Since the 2004 lockout, the Leafs have only made the playoffs once, in last year’s shortened season. Their drought seems destined to go on for a while.
1) Montreal Canadiens — 23 Stanley Cups (+1 pre-NHL)
The most storied franchise in hockey history, le Club de hockey Canadien. The Montreal Canadiens have 24 Stanley Cups in total, with their first coming in 1916, just one year before the NHL was formed.
The team is over 100 years old and has too many legends to count on fingers and toes. The team is not only the most successful franchise in hockey, but among the elite in all of sports.
You won’t see any division champion banners hanging in the Bell Centre. The Stanley Cup banners take up enough room.
Dynasties in the 1950s, 60s and 70s account for most of the cup wins, as the Habs won 16 of their 24 cups in those decades.
Cup wins in 1986 and 1993 rounded them out, but the franchise is currently in their longest drought between cups, with 21 years removing them from their last win.
While it is great to look back on the past of Howie Morenz, Maurice Richard, Jean Beliveau, Ken Dryden, Guy Lafleur, Larry Robinson, Patrick Roy and countless others, fans are now starved for cup no. 25. The Habs seem to be on their way, with a promising young core.
In the meantime, no team is catching them any time soon for the amount of championships they have.
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