Roy Massey spent a number of years working with Norwich City's youth teams; the latter role being based at the Potters Bar centre of excellent until it was closed due to FA rules about travelling times for young players. He left to join Arsenal's academy, taking with him the likes of Jay Simpson and Henri Lansbury

According to the Arsenal website, Roy’s day-to-day responsibility is to look after all of the Club’s youngsters at the Hale End Academy. In all there are almost 120 young footballers based at Hale End. He is also responsible for the recruitment of youngsters into the Academy.

As a player, Massey played as a centre forward for Rotherham United (1964-67), Leyton Orient (1967-69) and Colchester United (1969-71).He moved into coaching at Colchester Unied where he spent 15 years before joining Norwich.