 Initially educated at Tonbridge and Weymouth College, he entered Christ's College, Cambridge in 1897, where he was a football blue.Played football with his brother H W Masterman for amongst others Tunbridge Wells and is referred to in the "History of the Football Association" published in 1953 for an article he wrote in 1911 on the dispute between the Amateur Football Association and the Football Association.Served as a lieutenant in the 3rd Battalion Welsh Regiment in the Second Boer War, 1900–02; was made a captain in 1901.