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 finished off his career by playing professional football in Singapore with clubs such as Jurong, Balestier Khalsa and Tanjong Pagar United.
Masefield owns a company, Little League Malaysia 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 ESPN Star Sports coverage of the English Premier League.