10 Canadian NHL Teams That Won the Stanley Cup

Few trophies in sports carry the same weight and reverence as the Stanley Cup. Introduced in 1893, it represents the ultimate triumph in professional hockey, a symbol of endurance, teamwork, and national pride.

Canada’s relationship with the Cup runs deeper than any other nation’s.

The country gave birth to both the game itself and the National Hockey League, setting the stage for decades of fierce competition and celebrated champions.

Over the years, 22 Canadian teams have lifted the Cup, each leaving a lasting legacy on the sport.

However, today, we will focus on the top 10.

1. Montreal Canadiens

With 24 championships, they hold the record for the most Stanley Cup victories in history.

Their dynastic years between 1956 and 1960 saw five consecutive titles, followed by another remarkable run from 1976 to 1979.

Legendary figures such as Maurice “Rocket” Richard, Jean Béliveau, and Guy Lafleur defined eras of excellence.

The last triumph in 1993 remains historic – it marked the last time a Canadian team captured the Cup.

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2. Toronto Maple Leafs

Toronto’s hockey story carries both pride and pain. With 13 Stanley Cups, the Maple Leafs trail only Montreal in championships.

Their final victory came in 1967, the last season before the NHL expansion ended the “Original Six” era.

Since then, fans have endured the longest active championship drought in the league.

Despite this, names like Dave Keon, Johnny Bower, and Tim Horton still echo through hockey history, representing a golden age of Toronto’s dominance.

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3. Edmonton Oilers

During the 1980s, Edmonton redefined what offensive hockey could be.

Led by icons Wayne Gretzky, Mark Messier, and Paul Coffey, the Oilers captured five Stanley Cups between 1984 and 1990.

Their explosive style and unmatched talent turned them into a dynasty that revolutionized the game.

Even after Gretzky’s trade to Los Angeles, the team remained competitive, proving their depth and resilience under coach Glen Sather’s leadership.

For fans looking to celebrate that era of dominance or test their knowledge of the game, platforms like GG BET offer interactive ways to stay connected to the sport through hockey-themed games and entertainment.

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4. Calgary Flames

Calgary reached hockey’s pinnacle in 1989, clinching its only Stanley Cup by defeating the Montreal Canadiens in a rare all-Canadian final.

The team featured legends like Lanny McDonald, Joe Nieuwendyk, and goaltender Mike Vernon.

Their victory symbolized the strength of Western Canadian hockey and marked one of the most balanced rosters in league history.

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5. Ottawa Senators (Original Franchise)

Before folding in 1934, the original Ottawa Senators were a powerhouse of early NHL history.

Between 1920 and 1927, they secured four Stanley Cups, dominating with speed and skill unmatched in their era.

They played a central role in establishing professional hockey in Canada’s capital city.

Although the modern Senators share the name, the original team’s success remains a separate and glorious chapter of the sport.

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6. Montreal Maroons

Operating from 1924 to 1938, the Montreal Maroons offered English-speaking fans a rival to the Canadiens.

Their two Stanley Cup victories, in 1926 and 1935, showcased disciplined defense and innovative play.

Despite success, economic hardships led to their eventual dissolution.

Today, their legacy survives as a fascinating piece of Montreal’s hockey history.

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7. Vancouver Millionaires

The Vancouver Millionaires claimed the Stanley Cup in 1915, defeating the Ottawa Senators of that era.

The team, led by Fred “Cyclone” Taylor, became the first West Coast squad to bring the Cup home.

Although short-lived, their achievement remains a source of pride for British Columbia’s hockey fans.

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8. Quebec Bulldogs

Quebec City once fielded a hockey team that dominated the early 1910s. The Quebec Bulldogs captured consecutive Stanley Cups in 1912 and 1913 before joining the NHL briefly.

Financial struggles forced the franchise to relocate and rebrand as the Hamilton Tigers.

Despite a short existence, the Bulldogs’ victories cemented their status among Canada’s early hockey champions.

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9. Winnipeg Victorias

Winnipeg’s hockey roots reach back to the 19th century.

The Victorias claimed three Stanley Cups between 1896 and 1901, long before the NHL’s formation.

Competing in the amateur era, they helped shape early hockey rules and culture.

Their victories proved that Western Canada could rival Eastern teams even in hockey’s earliest days.

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10. Toronto Arenas / St. Pats

Before the Maple Leafs became a household name, Toronto’s franchise went through two identities: the Arenas and the St. Patricks.

As the Arenas, they won the Stanley Cup in 1918, the first year of NHL operation.

Four years later, the team captured another title as the St. Pats.

Eventually, they transformed into the Maple Leafs, carrying on Toronto’s championship tradition.

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The Drought: Canadian Teams Post-1993

Since Montreal’s victory in 1993, Canadian fans have endured decades without a championship.

Numerous close calls have teased hope:

Calgary in 2004, Edmonton in 2006, Vancouver in 2011, and Montreal again in 2021.

Economic factors, league expansion into U.S. markets, and salary cap dynamics have often favored American teams.

Despite these obstacles, Canadian teams continue to produce elite players and passionate fan bases that keep the dream alive.

Final Thoughts

Canadian hockey and the Stanley Cup are forever intertwined.

Every era of the sport owes something to the teams that brought glory to Canada’s rinks and cities.

Each championship echoes a story of pride, perseverance, and national passion.

Fans across the country still wait for the day the Cup returns home, knowing that Canada’s place in hockey history remains untouchable.