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.
Canadaโs relationship with the Cup runs deeper than any other nationโs.
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.
Team
Stanley Cup Wins
Most Recent Win
Montreal Canadiens
24
1993
Toronto Maple Leafs
13
1967
Edmonton Oilers
5
1990
Calgary Flames
1
1989
Ottawa Senators (original)
4
1927
Montreal Maroons
2
1935
Vancouver Millionaires
1
1915
Quebec Bulldogs
2
1913
Winnipeg Victorias
3
1901
Toronto Arenas/St. Pats
2
1922
1. Montreal Canadiens
No franchise in professional hockey has experienced dominance like the 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 โRocketโ Richard, Jean Bรฉliveau, 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.
Key Highlights:
2. Toronto Maple Leafs
Torontoโs 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 โOriginal Sixโ 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 Torontoโs dominance.
Key Highlights:
3. Edmonton Oilers
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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 Gretzkyโs trade to Los Angeles, the team remained competitive, proving their depth and resilience under coach Glen Satherโs 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.
Key Highlights:
4. Calgary Flames
Calgary reached hockeyโs 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.
Key Highlights:
5. Ottawa Senators (Original Franchise)
On this day in 1927, the original Ottawa Senators won their 10th and final Stanley Cup in front of 8,000 fans at the Ottawa Auditorium.
It was their fourth Stanley Cup in the 1920s. The 1926-27 team had seven Hall of Famers.
The NHL team folded in 1934. pic.twitter.com/tRaqp6TplDโ Craig Baird – Canadian History Ehx (@CraigBaird) April 13, 2024
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 Canadaโs capital city.
Although the modern Senators share the name, the original teamโs success remains a separate and glorious chapter of the sport.
Key Highlights:
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 Montrealโs hockey history.
Key Highlights:
7. Vancouver Millionaires
Vancouverโs hockey glory began long before the Canucks existed.
The Vancouver Millionaires claimed the Stanley Cup in 1915, defeating the Ottawa Senators of that era.
The team, led by Fred โCycloneโ Taylor, became the first West Coast squad to bring the Cup home.
Although short-lived, their achievement remains a source of pride for British Columbiaโs hockey fans.
Key Highlights:
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 Bulldogsโ victories cemented their status among Canadaโs early hockey champions.
Key Highlights:
9. Winnipeg Victorias
Winnipegโs hockey roots reach back to the 19th century.
The Victorias claimed three Stanley Cups between 1896 and 1901, long before the NHLโs 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 hockeyโs earliest days.
Key Highlights:
10. Toronto Arenas / St. Pats
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Before the Maple Leafs became a household name, Torontoโs 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 Torontoโs championship tradition.
Key Highlights:
The Drought: Canadian Teams Post-1993
Since Montrealโs 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 Canadaโs 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 Canadaโs place in hockey history remains untouchable.
