Arthur Howey Ross was a Canadian professional ice hockey player and executive from 1905 until 1954. Regarded as one of the best defenders of his era by his peers, he was one of the first to skate with the puck up the ice rather than pass it to a forward. He was on Stanley Cup championship teams twice in a playing career that lasted thirteen seasons; in January 1907 with the Kenora Thistles and 1908 with the Montreal Wanderers. Like other players of the time, Ross played for several different teams and leagues, and is most notable for his time with the Wanderers while they were members of the National Hockey Association (NHA) and its successor, the National Hockey League (NHL). In 1911 he led one of the first organized player strikes over increased pay. When the Wanderers' home arena burned down in January 1918, the team ceased operations and Ross retired as a player.

The Stanley Cup is the championship trophy awarded annually to the National Hockey League (NHL) playoff champion. It is the oldest existing trophy to be awarded to a professional sports franchise in North America, and the International Ice Hockey Federation (IIHF) considers it to be one of the "most important championships available to the sport". The trophy was commissioned in 1892 as the Dominion Hockey Challenge Cup and is named after Lord Stanley of Preston, the Governor General of Canada, who donated it as an award to Canada's top-ranking amateur ice hockey club. The entire Stanley family supported the sport, the sons and daughters all playing and promoting the game. The first Cup was awarded in 1893 to the Montreal Hockey Club, and winners from 1893 to 1914 were determined by challenge games and league play. Professional teams first became eligible to challenge for the Stanley Cup in 1906. In 1915, the National Hockey Association (NHA) and the Pacific Coast Hockey Association (PCHA), the two main professional ice hockey organizations, reached an agreement in which their respective champions would face each other annually for the Stanley Cup. It was established as the de facto championship trophy of the NHL in 1926 and then the de jure NHL championship prize in 1947.