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).
Five days later in the first Stanley Cup Finals game, the Montreal HC successfully defended their title with a 3–1 win over Ottawa.
Later in the year, the Cup trustees accepted a challenge from the squad from Osgoode Hall, the champions of the Ontario Hockey Association (OHA).
However, a challenge game was scheduled earlier for the next day between the previous year's champion Montreal HC and the squad from Queen's University, which was then part of the Ontario Hockey Association.
The Montreal Victorias won the 1896 AHAC title by finishing the season with a 7–1 record, and subsequently demanded a rematch for the Cup.
Another 7–1 record earned the Montreal Victorias the 1897 AHAC title, and the team subsequently received a challenge from the Ottawa Capitals, champions of the Central Canada Hockey Association (CCHA).
The defending Cup champion Montreal Victorias along with several other former AHAC members formed the Canadian Amateur Hockey League (CAHL).
In March, the Shamrocks finished the 1900 CAHL season in first place, and thus the league championship, with a 7–1 record and then received another challenge for the Cup.
The win earned the players the nickname of "Little Men of Iron" for their effort in holding off Winnipeg in the closing moments of game three.
In March, the 1903 CAHL season ended with the Montreal Victorias and the Ottawa Hockey Club tied for first place with identical 6–2 records.
As the new CAHL and Cup champions, the Ottawas accepted a challenge from the Rat Portage Thistles of the Manitoba & Northwestern Hockey Association (MNWHA).
In early March, the Montreal Wanderers of the Federal Amateur Hockey League (FAHL) challenged the Senators for the Cup.
On the same day that the third game of the Thistles - Ottawa series was played, the 1905 CAHL season ended with the Montreal Victorias winning the title.
For the 1905–06 season, the Ottawa HC (aka Silver Seven) joined the new Eastern Canada Amateur Hockey Association (ECAHA).
About a week later, Smiths Falls, the FAHL champions, issued a challenge for the Cup, but they suffered the same fate as Queen's University.
This was the first series in which professional players played for the Stanley Cup, as the Wanderers and other teams in the ECAHA were starting to mix amateurs with pros in their squads.
Aided by future Hockey Hall of Famers Tom Hooper, Tommy Phillips, and Art Ross, the Thistles came away with 4–2 and 8–6 victories for a combined score of 12–8 to win a two-game total goals series.
In March, Kenora would play and win the Manitoba Professional Hockey League (MPHL) playoffs against Brandon to successfully defend the Cup.
The Winnipeg Maple Leafs of the MHL challenged Montreal for the Cup in March, but the Wanderers came away with 11–5 and 9–3 wins to clinch the two-game total goals series, 20–8.
Montreal's greatest challenge happened two days later when they played a single-elimination game against the Toronto Professional HC.
Toronto was the champion of the newly established Ontario Professional Hockey League (OPHL), and was the first all-professional team to compete for the Cup.
While the Wanderers were forced to join the newly formed National Hockey Association (NHA), the defending Cup champion Ottawa HC still had to accept challenges.
In January 1910, they played a two-game total goals series against Galt, champions of the OPHL, but prevailed with 12–3 and 3–1 victories.
Soon after the Galt-Ottawa challenge series ended, the CHA folded because of financial difficulties, and Ottawa was admitted into the NHA.
Three days later, the Ottawas played the Port Arthur Bearcats of the New Ontario Hockey League (NOHL) in another one-game final.
The Bulldogs then went on to sweep the Moncton Victorias of the Maritime Professional Hockey League (MPHL) in a best-of-three Cup challenge series, with 9–3 and 8–0 victories.
In the first series ever between the champions of the two leagues, all of the games were played in Victoria, while the differing rules of the NHA and PCHA alternated between each contest.
At the end of the 1913–14 NHA season, the Toronto Hockey Club and the Montreal Canadiens were tied for first place with identical 13–7 records.
PCHA president Lester Patrick had not filed a challenge, because he had expected Emmett Quinn of the NHA to make all of the arrangements in his role as hockey commissioner, whereas the trustees thought they were being deliberately ignored.
Legend: SC = successful Stanley Cup challenge or defense of championship (win); UC = unsuccessful Stanley Cup challenge or defense of championship (loss) The following 16 teams unsuccessfully challenged for a Stanley Cup only once: Berlin Dutchmen, Dawson City Nuggets, Halifax Crescents, Moncton Victorias, Montreal Canadiens, New Glasgow Cubs, Ottawa Capitals, Ottawa Victorias, Port Arthur Bearcats, Smiths Falls, Sydney Millionaires, Toronto HC, Toronto Marlboros, Toronto Wellingtons, Victoria Aristocrats, Winnipeg Rowing Club.