NHL Teams with the Most Wins, as of 2021

1. Montreal Canadiens

Montreal Canadiens take home the cake with an overwhelming 24 Stanley Cup wins as of 2019, almost doubling Maple Leafs record.

2. Boston Bruins

3. Detroit Red Wings

4. Toronto Maple Leafs

5. New York Rangers

6. Chicago Blackhawks

7. Philadelphia Flyers

8. St. Louis Blues

9. Pittsburgh Penguins

10. Dallas Stars