Taylor started his professional career at Millwall where he played 28 games before being signed by Bolton for £150,000 in March 1996. Taylor failed to break into the Bolton side and only managed to score three goals in all competitions. One of these goals came in the memorable 6–1 League Cup win over Premier League side Tottenham Hotspur, when Bolton were in the second tier. After loan spells at Rotherham United and Blackpool, he signed for Tranmere Rovers in October 1998 for a fee of £350,000. Taylor played over 100 games for Tranmere in almost three years and played the full 90 minutes in the 2000 Football League Cup Final before signing for Stockport County on a free transfer in July 2001.