The Penguins have won five overall championships, but it's the Montreal Canadiens that have won the most Stanley Cups in the league's history.
The Habs have captured 24 Stanley Cups, with their last title coming in 1993. They also have the most appearance in the Final with 34.
The Toronto Maple Leafs have 13 championships, but their title drought dates back to 1967.
The current NHL teams have that not won a Stanley Cup title are the St. Louis Blues, Vancouver Canucks, Buffalo Sabres, Florida Panthers, Nashville Predators, Ottawa Senators, San Jose Sharks, Washington Capitals, Columbus Blue Jackets, Minnesota Wild and the Vegas Golden Knights.
The Blue Jackets, Wild and Golden Knights have never gone to a Stanley Cup Final.