Kenora Thistles
Donated in 1892 by Lord Stanley of Preston, the Governor General of Canada, the Stanley Cup was originally awarded to the top amateur team in Canada, who would then accept challenges from the winners of other leagues. From its inception until 1912, the Cup was nearly always won by teams from Montreal, Winnipeg, and Ottawa. In 1903 Ottawa won the Cup, after finishing the season tied for first in the Canadian Amateur Hockey League with the Montreal Victorias. They played a two-game, total-goal series for the league championship. The Montreal Hockey Club, who had held the Cup, finished third in the league and therefore lost the right to keep it.
Stanley Cup
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. However, in 1894, four teams out of the five-team AHAC tied for the championship with records of 5–3–0. The AHAC had no tie-breaking system. After extensive negotiations and Quebec's withdrawal from the championship competition, it was decided that a three-team tournament would take place in Montreal, with the Ottawa team receiving a bye to the final because they were the only road team. On March 17, in the first ever Stanley Cup playoff game, the Montreal Hockey Club (Montreal HC) defeated the Montreal Victorias, 3–2. Five days later, in the first Stanley Cup Final game, Montreal HC beat the Ottawa Hockey Club 3–1.
In 1895, Queen's University was the first official challenger for the Cup, although it was controversial. The Montreal Victorias had won the league title and thus the Stanley Cup, but the challenge match was between the previous year's champion, Montreal HC, and the university squad. The trustees decided that if the Montreal HC won the challenge match, the Victorias would become the Stanley Cup champions. The Montreal HC won the match 5–1 and their cross-town rivals were crowned the champions. The first successful challenge to the Cup came the next year by the Winnipeg Victorias, the champions of the Manitoba Hockey League. On February 14, 1896, the Winnipeg squad defeated the champions 2–0 and became the first team outside the AHAC to win the Cup.