He was a builder and sometimes player of the Ottawa Hockey Club, later to be known as the Ottawa Senators. With this club, he befriended the sons of Lord Stanley, the Governor-General of Canada. In 1892, Lord Stanley appointed him to be a trustee for his championship ice hockey trophy, known today as the Stanley Cup. He helped found the Ontario Hockey Association in 1890. He played in the first Ontario Hockey Association championship game in 1891 at the Rideau Rink in Ottawa, helping Ottawa win 5-0 over Toronto St Georges. Mr. Ross served as trustee for the Stanley Cup until his death in 1949.