Masterman was born in Wimbledon, London on 19 December 1876, the son of Thomas William Masterman. Initially educated at Tonbridge School 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.
Masterman, born in Wimbledon, London on December 19th, 1876, son of Thomas William Masterman, attended Tonbridge School and Weymouth College before entering Christ's College, Cambridge in 1897 where he was a football blue. He played football with his brother H W Masterman for teams like Tunbridge Wells. His work on the dispute between the Amateur Football Association and the Football Association was documented in the "History of the Football Association" published in 1953.