Beginnings
The first Stanley Cup may have been awarded in 1893, but the Montreal Amateur Athletic Association’s hockey club was actually established 1884.
It was only after years amateur competition that Frederick Stanley of the United Kingdom decided that the British Dominion in Canada needed a trophy which could be competed and challenged for.
The idea of awarding and challenging for the Cup meant that if your league - in this instance the AHAC - had awarded the trophy at the end of its season, another team could challenge for the Cup, and then their league would hold the trophy.
The first such challenge came in 1895 from Queen’s University. Which means that if they had successfully won their Stanley Cup challenge (they lost 5-1) the Cup would have then belonged to Queen’s University and the OHA.
A successful Stanley Cup challenge did happen in 1896 with the Winnipeg Victorias beating the Montreal Victorias, but by the end of the year the Montreal team had wrestled the Cup back. Which is the first instance of two Stanley Cup champions in one year.