[1][2] Three trustees were named to administer the trophy: Sir Edward Clouston, President of the Bank of Montreal, Dr. H. B. Yates of McGill University, (donor of the Yates Cup to the Intercollegiate Rugby Union in 1898) and Graham Drinkwater, four-time Stanley Cup champion.

After the season, the Cliffsides were defeated in the first-ever challenge by the Queen's University hockey club of Kingston, Ontario.

[citation needed] In the early years, trustees of the Cup quickly came to appreciate the difficulties of organizing a national competition in so large a country.

In 1914, at the suggestion of one of the trustees, Claude C. Robinson, the Canadian Amateur Hockey Association (CAHA) was formed as a national governing body for the sport with W. F. Taylor as its first president.

Starting in 1920, the Allan Cup champion team would represent Canada in amateur play at the Olympics and World Championships.

[10] The cancellation was caused by the reluctance to travel during wartime conditions, and the players' need to work rather than playing hockey.

The practice lasted from 1920 to 1964, when Father David Bauer established a permanent Canada men's national ice hockey team.

[13] The Cup championship is determined in an annual tournament held in the city or town of a host team, playing off against regional champions.