During the period from 1893 to 1914, the Stanley Cup was a "challenge trophy"; the champions held the Cup until they lost their league title to another club, or a champion from another league issued a formal challenge and subsequently defeated them in a special game or series. The competitive format of each challenge was determined by negotiation between the two clubs, and the contesting clubs did indeed make several arrangements during this 22-year period.

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.

Champions

Lord Stanley of Preston introduced the Stanley Cup in 1892 and it was first awarded at the end of winter 1893 to the league champion Montreal Hockey Club (Montreal HC). The same club won a playoff at the end of the 1894 season, which is considered the first "Stanley Cup challenge" although four clubs were involved in the process and three teams played games. Montreal HC lost the Cup by losing its league in 1895, decided early in March. The challenge system, as opposed to the Challenge Era, probably truly began sometime thereafter.

Season record 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.

Season Champion at end of season Other champion during season1892–93 Montreal HC 1893–94 Montreal HC 1894–95 Montreal Victorias Montreal HC 1895–96 Winnipeg Victorias 1896–97 Montreal Victorias 1897–98 Montreal Victorias 1898–99 Montreal Shamrocks Montreal Victorias 1899–1900 Montreal Shamrocks 1900–01 Winnipeg Victorias 1901–02 Montreal HC Winnipeg Victorias 1902–03 Ottawa HC Montreal HC 1903–04 Ottawa HC 1904–05 Ottawa HC 1905–06 Montreal Wanderers Ottawa HC 1906–07 Montreal Wanderers Kenora Thistles 1907–08 Montreal Wanderers 1908–09 Ottawa HC Montreal Wanderers 1909–10 Montreal Wanderers Ottawa HC 1910–11 Ottawa HC 1911–12 Quebec Bulldogs 1912–13 Quebec Bulldogs 1913–14 Toronto Blueshirts

Yearly record 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.

Year TimesCup Awarded Champions1893 1 Montreal HC 1894 1 Montreal HC 1895 2 Montreal Victorias Montreal HC 1896 3 Winnipeg Victorias Winnipeg Victorias Montreal Victorias 1897 2 Montreal Victorias Montreal Victorias 1898 1 Montreal Victorias 1899 3 Montreal Victorias Montreal Shamrocks Montreal Shamrocks 1900 3 Montreal Shamrocks Montreal Shamrocks Montreal Shamrocks 1901 1 Winnipeg Victorias Winnipeg Victorias 1902 2 Winnipeg Victorias Montreal HC 1903 3 Montreal HC Ottawa HC Ottawa HC 1904 4 Ottawa HC Ottawa HC Ottawa HC Ottawa HC 1905 3 Ottawa HC Ottawa HC Ottawa HC 1906 4 Ottawa HC Ottawa HC Montreal Wanderers Montreal Wanderers 1907 3 Kenora Thistles Kenora Thistles Montreal Wanderers 1908 5 Montreal Wanderers Montreal Wanderers Montreal Wanderers Montreal Wanderers Montreal Wanderers 1909 1 Ottawa HC 1910 4 Ottawa HC Ottawa HC Montreal Wanderers Montreal Wanderers 1911 3 Ottawa HC Ottawa HC Ottawa HC 1912 2 Quebec Bulldogs Quebec Bulldogs 1913 2 Quebec Bulldogs Quebec Bulldogs 1914 2 Toronto Blueshirts Toronto Blueshirts

1893–94 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.

Date Winning Team Score Losing Team LocationMarch 17, 1894Montreal HC3–2Montreal VictoriasVictoria Rink Date Winning Team Score Losing Team LocationMarch 22, 1894Montreal HC3–1OttawaVictoria Rink

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, the series was eventually cancelled because of the lack of ice.

1894–95 On March 8, 1895, the Montreal Victorias won the 1895 AHAC title and thus the Stanley Cup, after finishing the season with a 6–2 record. 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. Thus, it was decided that if the Montreal HC won the challenge match, the Victorias would become the Stanley Cup champions. The Montreal HC would eventually win the game, 5–1, and their crosstown rivals were crowned the champions.

Date Winning Team Score Losing Team LocationMarch 9, 1895Montreal HC5–1Queen's UniversityVictoria RinkMontreal Victorias wins the Cup based on winning the AHA title, and Montreal HC defeating Queen's University. Montreal HC were never recognized as Stanley Cup Champions in 1895, even though they won first challenge series from another hockey league.

Billy Barlow, the star player of Montreal was not able to play and Clarence McKerrow took his place. McKerrow had not played any games for Montreal, and could be considered a ringer, but there was no protest from Queen's.

The Queen's team, although described as looking fast in their tiger jerseys, were no match for Montreal and the game proved uninteresting.Coleman, p. 24

1895–96 The first successful challenge to the Cup came in February 1896 by the Winnipeg Victorias, the champions of the Manitoba Hockey Association (MHA). On February 14, Winnipeg beat defending champion Montreal, 2–0, becoming the first team outside the AHAC to win the Cup.

Date Winning Team Score Losing Team LocationFebruary 14, 1896Winnipeg Victorias2–0Montreal VictoriasVictoria Rink

1896–97 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. However, it was delayed until December 30 due to unsuitable ice conditions in Montreal. In what was said to be the most anticipated hockey game of the time, the Montreal Victorias defeated the Winnipeg Victorias, 6–5, to reclaim the Cup.

Date Winning Team Score Losing Team LocationDecember 30, 1896Montreal Victorias6–5Winnipeg VictoriasGranite Rink, Winnipeg

1897–98 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). It was originally scheduled as the first best-of-three challenge, but the series ended after the first game because the Victorias clearly was the superior team with a 15–2 victory.

Date Winning Team Score Losing Team LocationDecember 27, 1897Montreal Victorias15–2Ottawa CapitalsVictoria Rink

The Montreal Victorias again won the AHAC championship after finishing the 1898 AHAC season undefeated with an 8–0 record. As a result, no one challenged the Victorias for the Cup.

1898–99 Prior to the start of the 1898–99 season, the AHAC dissolved. The defending Cup champion Montreal Victorias along with several other former AHAC members formed the Canadian Amateur Hockey League (CAHL).

Montreal then received another challenge from the MHA's Winnipeg Victorias. This time, it was decided that they would play a two-game total goals series in February 1899.

The second game ended in controversy. With Montreal leading the game 3–2 with about 12 minutes left in the game, Montreal's Bob Macdougall violently slashed Winnipeg's Tony Gingras. As Gingras was carried off the ice, referee Bill Findlay only called Macdougall for a two-minute minor. Angry that he should have been accessed a larger penalty, Winnipeg went into their dressing room in protest. Insulted, Findlay abruptly went home, but returned after officials followed him on a sleigh and persuaded him to return. Once back at the rink, the referee gave Winnipeg 15 minutes to return to the ice themselves. They refused and thus Findlay disqualified the team and declared Montreal the winners.

Date Winning Team Score Losing Team LocationFebruary 15, 1899Montreal Victorias2–1Winnipeg VictoriasMontreal Arena, MontrealFebruary 18, 1899Montreal Victorias3–2Winnipeg VictoriasMontreal wins total goals series 5 goals to 3

Two weeks after the Montreal Victorias defeated Winnipeg in their two-game total goals series, they lost the 1899 CAHL title, and thus the Cup, to the Montreal Shamrocks. The Shamrocks compiled a 7–1 season record while the Victorias finished one game back at 6–2. The Shamrocks then played a challenge game against Queen's University on March 14, defeating them 6–2.

Date Winning Team Score Losing Team LocationMarch 14, 1899Montreal Shamrocks6–2Queen's UniversityMontreal Arena

1899–1900 The MHA's Winnipeg Victorias issued another challenge for the Cup. This time, a best-of-three series was played against the defending champion Montreal Shamrocks. Winnipeg won the first game, 4–3, but Montreal prevailed in the next two games, 3–2 and 5–4.

Date Winning Team Score Losing Team LocationFebruary 12, 1900Winnipeg Victorias4–3Montreal ShamrocksMontreal ArenaFebruary 14, 1900Montreal Shamrocks3–2Winnipeg VictoriasFebruary 16, 1900Montreal Shamrocks5–4Winnipeg VictoriasMontreal wins best-of-three series 2 games to 1

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. However, the Halifax Crescents of the Halifax City Hockey League (Maritime champions) did not pose much of a threat as Montreal crushed them, 10–2 and 11–0.

Date Winning Team Score Losing Team LocationMarch 5, 1900Montreal Shamrocks10–2Halifax CrescentsMontreal ArenaMarch 7, 1900Montreal Shamrocks11–0Halifax CrescentsMontreal wins best-of-three series 2 games to 0

1900–01 In January 1901, the Winnipeg Victorias again challenged the Montreal Shamrocks for the Cup. This time, Winnipeg prevailed, sweeping the best-of-three series with scores of 4–3 and 2–1. Game two was the first overtime game in Cup history with Dan Bain scoring at the four-minute mark of the extra period.

Date Winning Team Score Losing Team Location NotesJanuary 29, 1901Winnipeg Victorias4–3Montreal ShamrocksMontreal ArenaJanuary 31, 1901Winnipeg Victorias2–1Montreal Shamrocks4:00, OTWinnipeg wins best-of-three series 2 games to 0

1901–02 In January 1902, the OHA's Toronto Wellingtons challenged the Winnipeg Victorias for the Cup in a best-of-three series, but Winnipeg swept Toronto in two games with identical 5–3 scores.