The Toronto Maple Leafs have won the Cup 13 times. That is second to Montreal at 24.
New York Islanders
Liverpool have won 18 league titles!
Montreal Canadiens
the Montreal canadiens have won the most in the history of the nhl, but the nhl wasn't the only league that to compete for the cup.
The Montreal Canadiens have won the most games in the playoffs in NHL history.
The Montreal Canadiens with 24 (23 during the NHL era, and 1 win predates the NHL) are the winningest team in the NHL. The second most have been won by the Toronto Maple Leafs with 13, although they have not won since 1967.....
Real Madrid is the team that has won most La Liga titles with 32 titles. FC Barcelona are second with 21 titles.
Manchester United they won 19 premier league titles.
The Montreal Canadiens won the most championships in the NHL.
The St. Louis Cardinal won the second most world Series titles with 10.
Kurt angle has won 3 titles