Naylor had a trial with Leeds United in 1977, but did not sign for the club and the following year joined Yorkshire Amateur. He signed schoolboy forms with Lincoln City in February 1979 before turning professional in June 1980. During his time at Lincoln he spent time on loan at Kettering Town, Peterborough United and Crewe Alexandra. In February 1986 he moved to West Bromwich Albion for a £110,000 transfer fee. He also played for Bristol City, Mansfield Town (on loan), Exeter City and Rushden &amp; Diamonds, as well as winning three caps for the England B team. In May 1985 he was to witness a nightmare when 56 spectators were killed in a horrendous stand fire while playing for Lincoln against Bradford City.