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With the Edmonton Oilers looking to bring the Stanley Cup back to Canada for the first time since 1993, it’s the perfect time to take a look at which teams have won the coveted chalice the most times throughout NHL history.
It’s only fitting that it’s the Montreal Canadiens who have won the most Stanley Cups, as they are the aforementioned team to do so in 1993. While that makes them the most recent Canadian team to have hoisted Lord Stanley, it’s still been over three decades.
Regardless, they are well above the next-closest team, and the Habs won at least one Stanley Cup in every decade from when the title began (1910s) all the way through to the 1990s. The majority of those championships came between the 1950s and 1970s, and they have 34 Stanley Cup Final appearances in total. The most recent was in 2021, in which they lost to the Tampa Bay Lightning. Montreal is currently building around young talent such as Cole Caufield as they look to simply make it back to the postseason, let alone win their 25th Stanley Cup.
Behind the Habs, and well behind, is yet another Canadian team. Not only is it another team from the north, but it’s also one of the Original Six teams. That is certainly fitting for that original group to top this list.
However, it’s been tough sledding for the Leafs and the Toronto faithful. Their last Stanley Cup win came back in 1967, which was also the last time that they made the final series of the season. The 1960’s were incredible for them, as they won four titles in that decade. As for the 2000’s, it’s been quite the opposite. Toronto has won just one playoff series since 2004, and that was just a single round in the 2022-23 season. With such a high-payroll roster, expectations for the Leafs continue to be sky high.
Just south of the Canadian border is yet another Original Six team. They were also an incredible team of the 1960s, but were on the losing end of all four Stanley Cup Finals that they reached in that decade. As for their victories, it was the 1990s and early 2000s in which the Wings reigned supreme.
Four of their 11 titles came between 1997-2008, along with Stanley Cup Final appearances in both 1995 and 2009. In fact, they have even more appearances in total (24) than Toronto (21), but clearly, things haven’t always gone their way.
Heading east but still just as north brings us to Boston, as we continue the list of Original Six teams. They looked destined to make it seven titles following the 2022-23 season, as they set NHL records for wins (65) and points (135).
However, that season ended in a stunning first-round exit at the hands of the Florida Panthers. That means their last Stanley Cup win came in 2011, with two appearances since then, which came in 2013 and 2019.
In that 2013 Stanley Cup loss for the Bruins, it was the Chicago Blackhawks who came out victorious as they were in the midst of a dominant stretch. Of the ‘Hawks’ six titles, three of them came between 2010 and 2015. In fact, their 2013 championship was the last time Lord Stanley was hoisted by the Presidents’ Trophy winners. As of late, it’s been a struggle, but the 2023 #1 overall pick Connor Bedard has brought much hope that the franchise can return to prominence.
Lastly, we have two teams that are not a part of the Original Six but have equally incredible histories. Between the great Wayne Gretzky for the Edmonton Oilers and Jaromir Jagr for the Pittsburgh Penguins, their franchises are rich in records.
Mark has been a lifelong fan of all sports, and five years ago turned it into a profession, specializing in the NFL, NHL and MLB. He is a diehard Baltimore Ravens fan and has had his work published in sites such as Sports Illustrated, Pickswise and other top outlets.