Stanley Cup Winners: Teams with the Most Wins
If history is any guide, the Detroit Red Wings are more than familiar with what it takes to win the Stanley Cup. They’ve brought home the silverware 10 times, including three since 1996. The Pittsburgh Penguins have two Stanley Cups in franchise history and none since 1992.
Both teams have a lot of work to do before they catch up to the Montreal Canadiens. They have 24 Stanley Cups to their name, dating back to 1916 when the National Hockey Association was still trying to establish itself. The Habs would split from the NHA one year later with three other teams to form the National Hockey League.
The Red Wings might never catch Montreal. The Habs filled their trophy case during the Original Six era, taking advantage of their exclusive regional rights to Quebecois players like Maurice Richard and Jean Beliveau. But the second-place Toronto Maple Leafs and their 13 Cups (the last in 1967) are well within reach of the Red Wings.










