He went on to spend the next seven years at Vale Park, playing in the Anglo-Italian Cup final in 1996, as well as the club's Football League Trophy success in 2001.
Having caught the eye of Crewe Alexandra boss Dario Gradi, the 23-year-old striker completed an £11,000 switch to the "Railwaymen" in March 1990.
He scored a brace in a 3–1 win over Sunderland on 23 August 1997, showing his "sublime skill" as his "twinkling feet made them statuesque".
[11] He lost his first-team place in the 1999–2000 relegation season as new manager Brian Horton preferred Manchester United loanee David Healy.
[6] The club also managed to win the Football League Trophy in 2001, as they defeated Brentford 2–1 in the final at the Millennium Stadium in Cardiff; he won a penalty and also had a goal ruled out for offside.
[16] However, he was unable to prevent relegation the following season and was released at the end of the 2002–03 campaign after rejecting new manager Bobby Gould's new contract offer.
[5] Following a brief stay at Stone Dominoes,[17] Naylor joined Conference National club Telford United shortly into the 2003–04 campaign,[18] linking up with one of his strike partners from his Port Vale days in Lee Mills.
[12] Naylor quickly endeared himself to the supporters at the New Bucks Head[19] with his trademark pacey and tenacious displays particularly when he scored the second goal in a 2–1 victory of local rivals Shrewsbury Town in the FA Trophy.
Naylor joined his former club, Port Vale, in March 2005, now managed by his former strike partner Martin Foyle, but did not play a first-team game.
When an injury crisis hit the club, he donned his boots once more and scored twice from the penalty spot in a 2–2 draw at Frickley Athletic.