[9][14] Assuming the presidency of the Thunder Bay Amateur Hockey Association (TBAHA) during the 1918–19 season, Sterling felt that more organization was needed, including standardized rules and player residency requirements.

Prior to the 1919 annual meeting, he and secretary W. Harold Taylor revised the TBAHA constitution and by-laws to follow the framework of the Canadian Amateur Hockey Association (CAHA).

[16][21] The Port Arthur News-Chronicle wrote that the 1919–20 season was the "most satisfactory" to date, due to following the CAHA constitution and by-laws, with respect to player eligibility.

Trustee William Northey agreed to negotiate a deal, and to fund travel by the reigning 1920 Allan Cup champions Winnipeg Falcons to ice hockey at the 1920 Summer Olympics.

Although evidence would be difficult to find, he vowed to do everything in his power to ensure that the CAHA remained amateur and would investigate and suspend any player found to violate the rules.

The Winnipeg Tribune expected that the CAHA would introduce legislation which required transfers from one team to another, in an effort to reduce the number of players changing addresses three months prior to the start of the season.

McDiarmid refused to act on behalf of the CAHA since he felt it was not in his authority to do so,[29] which was interpreted by The Canadian Press that tourist players were welcomed in Manitoba.

[30] McDiarmid elaborated that each player on the Brandon Wheat City Hockey Club had established residency at least three months prior to the start of the season, and that he did not suspect there any other reason for the change of team.

[26] The detective also reported that former National Hockey League player Rusty Crawford was being paid $500 for the season, and that American Olympian Joseph McCormick declined an offer of $3,000 to play for the team.

[26] Sterling ordered the suspension of the Saskatoon team which was protested by the Saskatchewan Amateur Hockey Association (SAHA) as being unconstitutional since a vote of the CAHA executive was required.

[26] Sterling had returned to Winnipeg for his working career by 1921, and chose the city as the host location for the 1921 Allan Cup finals at an arena with an artificial ice surface.

[35] Sterling refused a request by McDiarmid and the MAHA for the suspended Saskatchewan team to be part of the playoffs as long as none of the players in question participated.

[38] In February 1921, the Calgary Regents Ladies Hockey Club wrote to Sterling seeking recognition by the CAHA and approval to enter tournaments.

[45] Nesbitt, Thomson and Company named Sterling the manager of an investment banking office established in Saskatoon, and he transferred him from Winnipeg in October 1927.

[49] In April 1939, eleven of thirteen CAHA past presidents including Sterling, were guests of honour at the association's silver jubilee held at the Royal Alexandra Hotel in Winnipeg.