In the storied history of the National Hockey League (NHL), the Stanley Cup stands as the ultimate symbol of hockey supremacy. Awarded annually to the league's playoff champion, it represents the culmination of a grueling season and a testament to a team's skill, determination, and teamwork. Originally donated in 1892 by Lord Stanley of Preston, the Governor General of Canada, the Stanley Cup is the oldest professional sports trophy in North America. From its early days as the Dominion Hockey Challenge Cup to its current status as the NHL's championship prize, the Stanley Cup has been won 109 times between 1915 and the end of the 2024–25 season. While 27 teams have claimed the cup, with 22 still active in the NHL, a select few franchises have etched their names into history with a remarkable number of victories.

Here's a look at the 10 NHL teams with the most Stanley Cups:

1. Montreal Canadiens (24): The Montreal Canadiens reign supreme as the most decorated team in NHL history, boasting an impressive 24 Stanley Cup championships. Their unparalleled success is a testament to their sustained excellence throughout the decades.

2. Toronto Maple Leafs (13): The Toronto Maple Leafs hold the second-highest number of Stanley Cup wins, with 13 championships. However, their last victory dates back to 1967, marking the longest active drought in the league.

3. Detroit Red Wings (11): The Detroit Red Wings have secured their place among hockey's elite with 11 Stanley Cup titles. Known for their skilled players and strong organizational culture, the Red Wings have consistently contended for championships throughout their history.

4. Boston Bruins (6): With a rich history dating back to the NHL's early years, the Boston Bruins have captured 6 Stanley Cups. Their passionate fanbase and iconic players have made them a perennial contender.

5. Chicago Blackhawks (6): The Chicago Blackhawks have experienced a resurgence in recent decades, adding to their historical success and bringing their Stanley Cup total to 6.

6. Edmonton Oilers (5): The Edmonton Oilers dynasty of the 1980s, led by Wayne Gretzky, contributed significantly to their 5 Stanley Cup victories.

7. Pittsburgh Penguins (5): The Pittsburgh Penguins have won 5 Stanley Cups. Between January 14, 1986, and January 14, 2026, the Pittsburgh Penguins have the most series wins by a team in the Stanley Cup Finals, with 5 wins.

8. New York Islanders (4): The New York Islanders dominated the early 1980s, capturing 4 consecutive Stanley Cups. This feat solidified their place in hockey history.

9. New York Rangers (4): The New York Rangers, with a long and storied history, have hoisted the Stanley Cup 4 times.

10. St. Louis Eagles (4): The St. Louis Eagles have 4 Stanley Cups. The original Ottawa Senators won the Stanley Cup in each of their four Final appearances (also 1922-23 and 1926-27).

It's worth noting that the Stanley Cup was not awarded in 1919 due to the Spanish flu pandemic and in 2005 because of the NHL lockout. The Florida Panthers are the most recent Stanley Cup champions, having won the trophy in 2024 and 2025.

The Stanley Cup continues to be the most sought-after trophy in professional hockey, and the teams that have won it multiple times hold a special place in the hearts of hockey fans worldwide.