A native of Belfast, Kyle was club secretary (overseeing the whole club including coaching/training) at Distillery in the Irish League from June 1897 to 1905. During this time the Whites claimed three League titles, two Irish Cups, one City Cup, three County Antrim Shields and one Belfast Charity Cup.
Kyle was invited to become secretary-managed at Sunderland in August 1905, remaining in the role until retiring on 15 March 1928. He thus remains Sunderlands longest serving "manager". During Kyle's time in charge Sunderland claimed the Football League title in 1913 and finished as runners-up in 1923. He is the only Irish manager ever to win the English top division.