In Manitoba, he sought to expand senior ice hockey and establish co-operation between teams and owners of the Winnipeg Amphitheatre on schedules and reducing travel costs.

He wanted all players aged 21 and younger to remain in junior ice hockey and began to negotiate with professional teams to refrain from signing them to contracts.

The relationship with the Maritimes worsened when the Halifax Wolverines were chosen to represent Canada at the Olympics but subsequently disbanded and their players removed from the national team after reports of demanding money.

Gilroy and the CAHA reached an agreement with the British Ice Hockey Association to halt the transfer of players from Canada to Great Britain until permission was granted.

On the eve of the Olympics, Gilroy allowed the two players to participate as a gesture of sportsmanship towards Great Britain, and objected to other countries portraying Canada as protesting the use of Foster and Archer.

[6] Notable players on his team included Ernie Dubeau, Jack Fraser, Newsy Lalonde, Skinner Poulin, Don Smith, and Cyclone Taylor.

[12] He was the purchasing manager for the Government of Manitoba for two years based in Winnipeg, then returned to Portage la Prairie operating a wholesale business from 1922 onwards.

[15] 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.

[17] 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.

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.

[19] 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.

[20] 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.

Gilroy named a committee to explore revisions to the MAHA constitution, and approved the University of Manitoba Grads to represent Canada at the 1931 Ice Hockey World Championships and a tour of Europe.

[34] Gilroy proposed to allow body checking by players of either team in either defensive zone to meet demands of modern spectators, but the rule change was defeated.

[40] In November 1932, Gilroy arranged for public meetings for the benefit of hockey players, coaches and referees, to clarify the rule change which now allowed the forward pass in the neutral zone.

[43] He also sat on the CAHA rules committee which decided to implement some of the changes made by the NHL, which included allowing the forward pass in all three zones, and body checking only to the puck carrier.

[48] The decision by players to migrate around the country looking for work was a result of the Great Depression in Canada, since more men sought to make a living by playing hockey.

[49] Gilroy asked the Maritime Amateur Hockey Association to "declare itself on the matter", with regards to operating a commercial league which was considered professionalism and not allowed under CAHA regulations or AAU of C by-laws.

[56] A three-team league was agreed upon in January, which included teams from Moncton, Halifax and Charlottetown operating under CAHA jurisdiction and excluding players who had not completed proper transfers.

[58] The Ontario Hockey Association (OHA) also sought to operate a commercial league for the 1934–35 season, and permission was granted by the CAHA with the stipulation that such teams followed proper registration and transfers regulations and would be ineligible for the Allan Cup playoffs.

[68] At the general meeting in 1935, the CAHA approved expenses to cover travel and equipment to send a team to Germany to represent Canada in ice hockey at the 1936 Winter Olympics.

[75] On January 7, 1936, the four members of the Halifax Wolverines that had been added to the national team, were removed after an emergency meeting in Toronto to deal with reports of them demanding money to take care of their families while they were overseas at the Olympics.

[77][79] The Maritime Amateur Hockey Association requested an official explanation of the dismissals from Gilroy and AAU of C president W. A. Fry, with suspensions forthcoming if the allegations were proven true.

Great Britain's manager Bunny Ahearne contested that international rules stated a player could leave a country without seeking permission, and the CAHA suspensions should not apply.

He admired Gilroy for his sportsmanship, but noted the choice to let Foster and Archer play did not make any friends, nor did the comment that senior amateur hockey in England was a "racket".

[107] Gilroy served as an alderman for the east ward of the Portage la Prairie municipal government for six years during the 1930s, and was an executive member of the local Board of Trade.

[108] The Winnipeg Free Press reported that the campaign for the seat vacated by Fawcett Taylor had few public meetings, no noticeable political issues being discussed, and appeared to be a popularity contest between Gilroy and Sexsmith.

[110] On June 25, Gilroy was nominated as the Liberal-Progressive Party candidate in the Portage la Prairie electoral district for the July 1936 Manitoba general election.

[116] Portage la Prairie was the only Canadian city at the time to have two former CAHA presidents as residents, in Gilroy and Sexsmith, who both participated in the ceremonial first puck at the new rink.

[128] Journalist Ralph Allen credited Gilroy with being progressive early in his presidency of the CAHA, for enforcing the rules and upholding the constitution to protect amateur hockey in Canada.