With a list of Stanley Cup winners and the year they won, you can see how many times a team has won the silver mug and sipped champagne from its bowl. There are three teams in NHL history to win the Cup more times than all the others. They are the Montreal Canadians who have won the Stanley Cup 24 times since the 1915-16 season. The Toronto Maple Leafs have won the Stanley Cup 11 times since the 1931-32 season and the Detroit Red Wings have won the Stanley Cup 11 times since the 1935-36 season.
Before 1968 the original six teams played 70 games in the regular season, with a format of, the top four teams playing for the Stanley Cup. Just two rounds of playoffs with a best of seven series to win the Cup.
In 1974-75, after a 78 game regular season, four divisions qualified for the playoffs. The number one team of each division would sit back and wait for the other eight teams to playoff a best of three series, then to advance to play with the number one teams in a best of seven series, then to advance to the last four teams remaining to play a best four out of seven series to meet in the final series. Add on another seven games if it should take that many to win the Stanley Cup, you could have a possible 24 games to play!
In todays NHL, out of 30 teams, six divisions and two Conferences, 16 teams qualify for the playoffs in a best of seven format. 21 games for the Stanley Cup winner are possible if all three series go the distance of seven games each.