NHL fans betting on their favorite team have been rooting for a Stanley Cup victory in the NHL since 1926. Prior to becoming the grandest prize for the NHL, fans betting on the victor of the Stanley Cup had a wide variety of leagues to cheer and choose from when determining a champion. Before becoming sole property of the NHL in 1926, the Stanley Cup was commonly known as the Challenge Cup. Although being donated by the 1892 Governor General of Canada, Lord Stanley of Preston, the Cup did not actually receive the Stanley Cup name until 21 years after the NHL became its sole proprietor, in 1947.

The first known Stanley Cup was awarded in the 1894 to 1895 season as the Montreal Hockey Club, defeated the Ottawa Generals three to one in the championship game. From that season to 1918, the Stanley Cup was awarded each year to the winner of the challenge cup series. The challenge cup series was played amongst the champions of different leagues including teams from the NHL. However in 1919 the Montreal Canadiens of the NHL and the Seattle Metropolitans had to cancel their series because of an outbreak of Spanish Flu. Prior to folding the 1924-25 Victoria Cougars of the WHL were the last non-NHL franchise to win the Stanley Cup, as they had defeated the Montreal Canadiens.

Before expanding to 12 teams in 1967, the Stanley Cup was fought over by the original six NHL franchises, the Boston Bruins, Chicago Blackhawks, Detroit Red Wings, Montreal Canadiens, New York Rangers and Toronto Maple Leafs. Each of the six teams was made up of the best players in the world, which at the time was dominated by American and Canadiens. Of the Six teams, the two Canadian franchises, Toronto and Montreal won the most Stanley Cups, with Detroit winning the third most, while Chicago and Boston were each the two poorest teams.