Interest in ice hockey at the Victoria Skating Club in Montreal, dates to at least 1874, and is attributed to the efforts of James Creighton then a judge of skating at the club, in organizing his friends to play on the rink with sticks and skates from his home province of Nova Scotia. In 1875, the first recorded organized hockey game took place at its rink, the Victoria Skating Rink, which had opened in 1862, between skating club members and McGill University students. Until 1883, there was only exhibition matches against other teams in Montreal. Tournaments would begin in 1883 at the Montreal Winter Carnival.
On January 10, 1882, the Victoria Hockey Club held what was described as its 'first annual meeting', whereby it elected its president James G. Monk. Other directors included George W. Gardner as vice-president, secretary-treasurer was Charles Lamothe. Hockey was played with both balls and pucks during this period. According to McGill hockey club member W. L. Murray, by 1881 it was normally played with a square puck, made by slicing a rubber ball. According to Murray, the Victoria club of the 1880s is credited with eliminating the square edges and playing with a round puck.
In 1886, the club helped to found the Amateur Hockey Association of Canada (AHAC). The team played in this league from 1887-1898. It was during this period that the team had its greatest success, winning the Stanley Cup in 1895, December 1896, 1897, 1898 and February 1899. They also won the AHAC league in 1895, 1896, 1897 and 1898. In 1894, the team participated in the first Stanley Cup playoff, losing 3–2 to Montreal in the semi-final.
The team resigned from the AHAC in 1898 over the proposal to allow the Ottawa Capitals into the league, and helped form the Canadian Amateur Hockey League (CAHL) in which they played from 1899-1905. The CAHL itself folded in 1905 and the team helped found the Eastern Canada Amateur Hockey Association. The league allowed amateurs and professionals to play against each other openly. The Victorias played in the league for two years as a purely amateur team leaving the ECAHA after the 1908 season to focus on amateur play.