Career
Masefield started his career in the youth ranks alongside Alan Shearer at Southampton. However, he signed his first professional contract with Birmingham City and in spite of being with the club for four years (including a year with the first team), he never made a first team appearance. After brief spells with Cheltenham Town and Exeter City (on a non-contract basis), he then moved to Stockport County and Doncaster Rovers, for whom he played seven and nine matches respectively.
He then played six games for Preston North End alongside future Everton manager David Moyes.
He had brief spells at Bromsgrove Rovers and Limerick, with whom he was player-coach between September and November 1994. He then moved to Hong Kong, where he played for the Sing Tao Sports Club, as well as for a Hong Kong league All-Star team and although he never represented the official Hong Kong national side, he did take on the likes of Sampdoria, Inter Milan and the Yugoslavian national side in unofficial matches.
Masefield owns a company that runs a coaching school for children, which attracts as many as 3000 subjects per year. He has coached Singapore Cricket Club in the second tier of Singaporean football, and is also a pundit on the Entertainment and Sports Programming Network Star Sports coverage of the English Premier League.He also features in isl star sports post coverage.