Crewe Alexandra Naylor began his career at
non-League Droylsden. 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. His new club went on to be
relegated at the end of the season, however, Naylor helped Crewe to the
Fourth Division play-offs in 1991. Promotion finally came in
1993–94, as Naylor's goals helped to assure Alex of the third automatic promotion place.
Port Vale On 14 July 1994, Naylor joined
Port Vale on a three-year contract for a fee of £150,000 that was agreed to avoid Vale and Crewe undergoing a transfer tribunal.
John Rudge's "Valiants" spent the money after sealing
promotion from the
Second Division on the last day of the
1993–94 season. Naylor would join the side for the new season in the
First Division. He soon formed a very effective strike partnership with
Martin Foyle. He was with the "Valiants" through one of the club's
most successful periods as they finished eighth in the
1996–97 First Division (the club's highest finish since the 1930s), with Naylor claiming 20 goals in 49 appearances, including a
hat-trick past
Charlton Athletic whilst playing as a lone striker in a 3–1 win at
The Valley on 14 December After the match he said he hated playing as a lone striker but conceded that "it worked ok today". In total, he managed to notch 90 goals in his seven years at the club, finishing as the club's
top goalscorer at the end of the
1995–96, 1996–97 and
2000–01 seasons with 12, 20 and 21 goals respectively. 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". He nutmegged
Andy Melville on a run that began just inside the Sunderland half and ended with a swerving right-foot shot into the corner of the net. He lost his first-team place in the
1999–2000 relegation season as new manager
Brian Horton preferred
Manchester United loanee
David Healy. He regained his place in the
first XI in the
2000–01 campaign, when he formed a strike partnership with
Steve Brooker and scored 20 goals. Naylor's last goal for the club was also the last goal at
Oxford United's
Manor Ground in May 2001. Naylor left the club after rejecting a two-year
contract that would see him take a 40% pay cut. His goals guided the Robins to promotion to
League One, via the
play-offs, in his first season. He started in
the final, a 3–1 victory over
Rushden & Diamonds. It was the first time Cheltenham had been that high in the
Football League pyramid.
Manager Steve Cotterill was keen to praise Naylor, as was his successor
Graham Allner. 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. Naylor joined
Conference National club
Telford United shortly into the
2003–04 campaign, linking up with one of his strike partners from his Port Vale days in
Lee Mills. 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 eventually made 29 appearances during the season, scoring 11 goals. Despite helping Telford to reach the fourth round of the
FA Cup and the semi-finals of the
FA Trophy, United were beset by off the field problems during the final few months of the 2003–04 season and folded at the end of the campaign after their finances spiralled out of control. Naylor was again on the lookout for a new club and was linked with a move to Shrewsbury Town after his impressive displays against them for Telford, but this never materialised. After several fruitless trials, he eventually retired from the professional game.
Later career 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. ==Style of play==