List of Stanley Cup challenge games

During the period from 1893 to 1914, the Stanley Cup was a "challenge trophy"; the champions held onto the Cup until they either lost their league title to another club, or a champion from another league issued a formal challenge and subsequently defeated the reigning Cup champion in a special game or series. The playoff format for each challenge varied depending on what the two competing clubs agreed to.

Before 1912, challenges could take place at any time, given the appropriate rink conditions, and it was common for teams to defend the Cup numerous times during the year. In 1912, the Cup's trustees declared that the Cup was only to be defended at the end of the champion team's regular season.

Also during this era, all of the leagues that played for the trophy had no annual formal playoff system to decide their own respective championships; whoever finished in first place after the regular season won the league title. Thus, a few league championship games or series were held just to break first place ties and determine who would keep the Cup. These league title games have historically been listed along with the regular inter-league Cup challenges.

This table lists all the champions of the Stanley Cup per hockey season during the challenge era. A season did not have official dates as rinks were natural ice, so season roughly corresponds to winter. The leagues typically started close to the beginning of the calendar year and ended in early March.

This table lists all the champions of the Stanley Cup per year during the challenge era. Annual Stanley Cup Final series did not begin until 1915, before which time there often were two different champions in a single year, and as many as five different championships.

The first Stanley Cup playoff game occurred on March 17, 1894. At the end of the Amateur Hockey Association of Canada season, four teams tied for the AHAC championship with records of 5–3–0. This created problems for the AHAC governors and the Cup's trustees since there was no tiebreaking system in place. After long negotiation and the withdrawal of Quebec from the championship situation, it was decided that a three-team tournament would take place in Montreal, with the Ottawa Hockey Club getting a bye to the finals (being the sole "road" team). In the first Stanley Cup playoff game ever, the Montreal Hockey Club defeated the Montreal Victorias, 3–2. Five days later in the first Stanley Cup Final game, the Montreal HC successfully defended their title with a 3–1 win over Ottawa.

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