Rubuta ci gaba don wannan sakin layi - Naylor yana da gwaji tare da Leeds United a 1977, amma bai sanya hannu a kulob din ba kuma a shekara mai zuwa ya shiga Yorkshire Amateur. Ya sanya hannu kan takardun makaranta tare da Lincoln City a watan Fabrairun 1979 kafin ya zama kwararre a watan Yunin 1980. A lokacin da yake a Lincoln ya ciyar da lokaci a kan aro a Kettering Town, Peterborough United da Crewe Alexandra. A watan Fabrairun 1986 ya koma West Bromwich Albion don kuɗin canja wuri na £ 110,000. Ya kuma buga wa Bristol City, Mansfield Town (a aro), Exeter City da Rushden & Diamonds, tare da lashe wasanni uku don tawagar Ingila B. A watan Mayun 1985 ya shaida mafarki mai ban tsoro lokacin da aka kashe 'yan kallo 56 a cikin mummunar wuta
yayin da yake buga wa Lincoln wasa da Bradford City.