Manitoba Amateur Hockey Association (MAHA), and sat on the executive committee of the Portage la Prairie minor ice hockey league. As Portage Hockey Club president, he was appointed by the MAHA to committee to oversee the Manitoba Senior Hockey League. He noted the team had strong support from Portage la Prairie which allowed it to grow and prosper, and advocated to find non-hockey employment for players to keep them local instead of transferring elsewhere. Gilroy was elected president of the MAHA in November 1927, to succeed newspaper executive A. E. H. Coo. A letter from Gilroy was published in the Winnipeg Free Press in December, in which he reiterated his commitment to expanding senior ice hockey in Manitoba, and restoring it to the prominence it had before rosters were depleted by professional teams. He was open to university teams participating in the Manitoba Senior Hockey League, wanted to work with owners of the Winnipeg Amphitheatre on schedules, and address concerns of attendance figures and travel costs to games outside of Winnipeg. He also sought to keep teams based in the MAHA as opposed to playing in neighbouring districts such as the Thunder Bay Amateur Hockey Association (TBAHA). The 1927–28 season had the greatest number of hockey teams in Manitoba at the time, with the most growth in rural areas. Gilroy advocated for support of leagues based in rural areas to grow interest in the game, and since those teams could not raise funds to travel long distances to play in larger cities. He wanted to shorten the provincial playoffs system which extended play into poor ice conditions later in the season. As growth increased, he sought to educate teams and players in Manitoba that registration requirements including transfers between clubs would be enforced in the 1928–29 season, and published letters in newspapers advising of changes to consistent with new amateur regulations across Canada. The MAHA implemented upper and lower divisions in the Manitoba Senior Hockey League for the 1929–30 season, and received more applications from teams in Winnipeg than ice availability could support. The MAHA arranged for all of the upper division teams to play in Winnipeg to reduce travel costs, and expanded the lower division with teams from Brandon, Elkhorn, Souris, and Virden. Gilroy's desire to shorten the playoffs was realized when national deadlines were imposed. The MAHA sought for all players aged 21 and younger to remain in