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 have 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.
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 Fame names 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.
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.
Hockey's Biggest Rivalry
Something Bruins fans really enjoy telling Montreal fans is that the Canadians have not won a Stanley Cup since 1992. The Montreal Canadians - Boston Bruins rivalry is one of the most intense in sports. They firsted faced off with each other in a game in 1924. Both teams have met since then in 34 playoff series games 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 legendary hockey games.
The Greatest Trophy in Sports.
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.
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. It looks like the Stanley Cup will be awarded in 2020 though, so take that Coronavirus.
Noel James Riggs, Madrid Spain.
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.