The Top 5 NHL Teams with the Most Stanley Cups

  NHL Team Stanley Cup Wins Years in League
1 Montreal Canadiens 24 104
(1918 - 2022)
2 Toronto Maple Leafs 13 104
(1918 - 2022)
3 Detroit Red Wings 11 95
(1927 - 2022)
4 Boston Bruins

Chicago Blackhawks
6 each 97
(1925 - 2022)
(1926 - 2021)
5 Edmonton Oilers

Pittsburgh Penguins
5 each 42
(1980 - 2022)
(1967 - 2021)
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 Special Report

What you'll learn in this report:

  • The most Stanley Cup wins record will probably never be broken.
  • 70's hockey was pretty awesome.
  • The Boston Bruins hate The Montreal Canadiens and vice versa.

  • And much, much more...

    The Greatest Hockey Dynasty Ever

    The question of who has the most Stanley Cups is an easy one to answer. It's the team that has been around longer than the NHL itself. The Montreal Canadiens. They have by far, the most Stanley Cup wins at 24. The Montreal Canadiens have appeared in the Stanley Cup Finals an astonishing 34 times and they hold the record for the most appearances in the finals by any team in the NHL.

    The Canadiens or as the franchise is officially known, "Le club de hockey Canadien" was founded in 1909-1910 making them the oldest team in professional hockey. In fact, they've been around so long and won so many Stanley cups that fans of other teams hate them. Especially Boston fans. That's okay, because no team will catch up to their Stanley Cup wins anytime soon.

    Here are all the years they've won:

    1915–16, 1923–24, 1929–30, 1930–31, 1943–44, 1945–46, 1952–53, 1955–56, 1956–57, 1957–58, 1958–59, 1959–60, 1964–65, 1965–66, 1967–68, 1968–69, 1970–71, 1972–73, 1975–76, 1976–77, 1977–78, 1978–79, 1985–86, 1992–93.
    The Stanley Cup
    This is the smile of a winner.

    Those 70's Canadiens

    In the 1970s the Montreal Canadiens won 4 Stanley Cups in a row with Scotty Bowman as their coach in 1976, 1977, 1978, and 1979. The Bowman team is considered to be one of the greatest teams in NHL history with Hockey Hall of Famers on the roster such as Guy Lafleur, Ken Dryden, Larry Robinson and Steve Shutt. 9 of the players from that team would later enter the Hockey Hall of Fame including coach Bowman

    Montreal Guy Lafleur
    70's poetry in motion.

    Another amazing hockey achievement was the 1943/1944 season, the Canadiens were nearly unbeatable during that time, losing only five games in the entire 50 games they played that year, and they kept winning through to the playoffs to take home the cup. The team also has the record for most consecutive Stanley Cups, winning five straight through 1956, 1957, 1958, 1969, and 1960.

    The Stanley Cup
    This guy might have had something to do with that.

    Hockey's Biggest Rivalry

    Something Bruins fans really enjoy telling Montreal fans is that the Canadians have not won a Stanley Cup since 1992. Probably because they are a teensy bit jealous of Montreal's pretty much unshatterable record of Stanley cup wins. As you've probably guessed by now, the Montreal Canadians - Boston Bruins rivalry is one of the most intense in all of sports. They first faced-off with each other in a game in 1924. Both teams have met in 34 playoff series games since then for a total of 177 games. The Canadiens have won 469 of all the games they've played together, and the Bruins have won 345. Their rivalry is so intense that it once started a riot. Their rough and tumble brand of play together has led to some exciting and legendary hockey.

    Montreal and Boston
    Montreal and Boston Goalies paying their respects to each other.

    The Greatest Trophy in all of Sports.

    That's right. We said it. The Stanley Cup is the greatest (and most handsome) trophy in all of sports. We dare you to find a more coveted, more historic trophy anywhere. In fact, we double dare you.

    There have only been four official engravers of the Stanley Cup. The first engravers comprised of two generations of the Peterson family, with assistance from Fred Light Sr. They were followed by Doug Boffey, owner of Boffey Silversmiths of Montreal. The current engraver is Louise St. Jacques, who took over Boffey's engraving business and left the legacy of the shop's name in place.

    The first team to have its roster engraved on the Stanley Cup were the 1906-07 Montreal Wanderers. The first woman to be engraved on the cup was Marguerite Norris, the then President of the Detroit Red Wings from 1954 & 1955. There are currently 16 women with their names on the Stanley Cup.

    Marguerite Norris Stanley Cup
    Stand aside boys, this one's mine.

    There are actually three Stanley Cups: the original bowl, the authenticated Cup, and the replica at the Hall of Fame. The original bowl, purchased by Lord Stanley and physically awarded to the champion for the first 71 years of competition, is currently displayed at the Hockey Hall of Fame in Toronto, Ontario.

    The original Stanley Cup bowl was made of silver and has a dimension of 18.5 centimetres (7.28 inches) in height and 29 centimetres (11.42 inches) in diameter.

    The current Stanley Cup, topped with a copy of the original bowl, is made of silver and nickel alloy. Nowadays the Stanley Cup has a height of 89.54 centimetres (35.25 inches) and weighs 15.5 kilograms (34.5 lb).

    Not only is it the oldest championship trophy to still be awarded today, but it is also the most valuable trophy in sports, with an estimated value of USD 650,000 (around $26.00 Canadian); although we here at seriously think it would fetch USD 1 Billion if it were to come up in the auction. Maybe you can tell we're hockey fans.

    The Stanley Cup of Hockey
    We dare you to say this isn't worth a billion dollars...

    Yes, that's "Lord" Stanley to You Sir

    The Stanley Cup is named after "Lord Stanley of Preston" a governor-general of Canada who created the trophy in 1892. It was awarded for the first time in 1893 to Montreal HC. In 1915. Before that, it was known as the Dominion Hockey Challenge Cup. We sincerely doubt that any other important North American sports trophy is named after a lord. Take that basketball.

    Montreal and Boston
    His stick-handling was magic to behold

    A Virus Stops the Game.

    In 1919, something happened that we can all identify with today, the Spanish influenza epidemic raging across the world at the time, forced the Montreal Canadiens and the Seattle Metropolitans to cancel their series, marking the first time the Stanley Cup was not awarded. Despite the pandemics best efforts the Stanley Cup was awarded in 2020 though, so take that Coronavirus.

    The Montreal Canadiens were in the 2021 Stanley Cup Finals!!

    What? The Montreal Canadiens were in the Stanley Cup finals in 2021 after beating the Vegas Golden Knights in overtime...wait, when did Las Vegas get a hockey team? The T5OA office went nuts when Lehkonen put the puck in for Montreal in overtime. I've personally never seen so much joy at the office (hey get back to work everybody). Anyway, fingers were crossed here at We dared to dream, after all, a team can come back from being down 3-0 and win 4 straight right?

    Nope. It turns out they can't. Congrats go to the Tampa Bay Lightning for their second Stanley Cup in as many years. That's actually pretty awesome. Only 22 more Stanley Cups to go to catch up to Montreal.

    Noel James Riggs Noel James Riggs,
    Owner and Head Writer, Top 5 of
    Contact me at:
    Top 5 Special Report sources:
    a. Hockey Hall of Fame and Museum,
    b. The Wall Street Journal: "The Stanley Cup Could Use an Editor" by Reed Albergotti.

    Tags: Sports Statistics, Top 5 Most

    Sources:  Top 5 of Anything Sports Research Team 2022.

    List Notes: Data is NHL teams with the most Stanley Cup wins. NHL season ending in 2021. Please note: this list includes Stanley Cup wins by teams while in the NHL only.
    NHL Teams with the Most Stanley Cups

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