From 1914 to the end of the 2017 season, the trophy has been won 99 times. 23 different teams have won the cup, 18 of which are still active in the NHL. Prior to that, the challenge cup was held by nine different teams. The Montreal Canadiens have won the Stanley Cup 24 times and made the finals an additional ten times. There were two years when the Stanley Cup was not awarded: 1919, because of the Spanish flu epidemic, and 2005, because of the NHL lockout.
which canadian hockey team has won the most stanley cups
Montreal Canadiens