<P> From 1914 to the end of the 2018 season, the trophy has been won 100 times . 24 teams have won the cup, 19 of which are still active in the NHL . Prior to that, the challenge cup was held by nine 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 . </P> <P> The origins of the Challenge era come from the method of play of the Amateur Hockey Association of Canada prior to 1893 . From 1887 to 1893, the league did not play a round - robin format, but rather challenges between teams of the association that year, with the winner of the series being the' interim' champion, with the final challenge winner becoming the league champion for the year . The Stanley Cup kept the tradition going, but added league championships as another way that a team could win the trophy . If a team in the same league as the current champion won the league championship, it would then inherit the Cup, without a challenge . The only time this rule was not followed was in 1904, when the Ottawa Senators club withdrew from its league, the CAHL . The trustees ruled that the Cup stayed with Ottawa, instead of the CAHL league champion . </P> <P> During the challenge cup period, none of the leagues that played for the trophy had a formal playoff system to decide their respective champions; whichever team finished in first place after the regular season won the league title . A playoff would only be played if teams tied for first - place in their leagues at the end of the regular season . Challenge games were played until 1912 at any time during hockey season by challenges approved and / or ordered by the Stanley Cup trustees . In 1912, Cup trustees declared that it was only to be defended at the end of the champion team's regular season . </P> <P> In 1908, the Allan Cup was introduced as the trophy for Canada's amateurs, as the Stanley Cup became a symbol of professional hockey supremacy . </P>

How many teams won 3 stanley cups in a row