He made a total of 386 appearances in the Football league for Crystal Palace, West Ham United, Fulham and Portsmouth.
Starting as an amateur footballer aged sixteen,[3] Stephenson signed professional terms on 15 February 1962[2] and made his senior debut for Crystal Palace as a seventeen-year-old on 24 March 1962.
He was appointed as captain by manager Dick Graham and from 1964, rarely missed a game playing alongside Brian Wood.
Stephenson failed to solve the defensive problems which had existed since the departure of Ken Brown in 1965 and, following a loan spell for Fulham in season 1971–72, he was transferred for £32,000 to Portsmouth for whom he made 98 appearances until 1975.
[3][7] He coached their reserve team but after four years with Orient, quit football to run a pub in Colchester[3] and to work as an education and welfare officer with Essex County Council.