The quest for the Stanley Cup, the oldest trophy in North American professional sports, is a grueling test of skill, endurance, and teamwork. Originally awarded in 1893 to the top hockey club in Canada, it has been presented to the National Hockey League (NHL) champion since 1926. Winning the Stanley Cup is the ultimate goal for every NHL team, and some franchises have achieved this pinnacle of success more often than others. Here's a look at 10 NHL teams that have hoisted the Stanley Cup the most times:

1. Montreal Canadiens (24): The Montreal Canadiens stand alone as the most successful team in NHL history, with a record 24 Stanley Cup victories. Their dynasty years in the mid-20th century cemented their place in hockey lore, and they have produced some of the game's greatest players. The Canadiens' last Stanley Cup win came in 1993. The franchise has also appeared in the Stanley Cup Final 35 times.

2. Toronto Maple Leafs (13): The Toronto Maple Leafs hold the second spot with 13 Stanley Cup wins. While their last championship dates back to 1967, their early dominance helped establish the team as a cornerstone of the NHL. The Maple Leafs remain one of the most popular and valuable franchises in the league.

3. Detroit Red Wings (11): The Detroit Red Wings, affectionately known as "Hockeytown," have captured 11 Stanley Cups. Their consistent success throughout the decades, including multiple championships in the late 1990s and early 2000s, has solidified their place among the NHL's elite.

4. Boston Bruins (6): The Boston Bruins, one of the Original Six teams, have a long and storied history, marked by six Stanley Cup victories. Known for their passionate fan base and fierce competitiveness, the Bruins have consistently been a force in the NHL. The Bruins have made 20 Stanley Cup appearances.

5. Chicago Blackhawks (6): The Chicago Blackhawks have also won 6 Stanley Cups. The Blackhawks saw a resurgence in the 21st century, capturing three Stanley Cups in 2010, 2013, and 2015.

6. Edmonton Oilers (5): The Edmonton Oilers won five Stanley Cups between 1984 and 1990. Led by Wayne Gretzky, the Oilers were known for their high-octane offense and revolutionized the game with their speed and skill.

7. Pittsburgh Penguins (5): The Pittsburgh Penguins have also won five Stanley Cups. The Penguins' success has been driven by superstars like Mario Lemieux and Sidney Crosby, who have led the team to multiple championships.

8. New York Rangers (4): Another of the Original Six, the New York Rangers have hoisted the Stanley Cup four times. Their rich history and presence in a major media market make them one of the league's most prominent franchises. The Rangers have made 11 Stanley Cup Finals appearances.

9. New York Islanders (4): The New York Islanders won four consecutive Stanley Cups from 1980 to 1983. This dynasty, led by players like Mike Bossy and Denis Potvin, left an indelible mark on the NHL.

10. New Jersey Devils (3): The New Jersey Devils have secured three Stanley Cup titles, establishing themselves as a perennial contender in the Eastern Conference.

The Modern NHL

In recent years, the NHL has seen new teams rise to prominence. The Florida Panthers became the latest team to win the Stanley Cup, securing back-to-back titles in 2024 and 2025. Their recent victories highlight the ever-changing landscape of the NHL, where new contenders can emerge and challenge the established powers. Several teams are making moves to improve their rosters, including the Colorado Avalanche signing Brent Burns, the New York Rangers acquiring Ryan Lindgren, and the Calgary Flames extending Morgan Frost's contract. These transactions demonstrate the ongoing efforts of teams to compete for the ultimate prize.