Taylor made his Bolton debut on 10 January 1998 in a 0–0 draw with Southampton. He played four times for the club during his initial month-long spell on loan, scoring once. The goal came in the fourth and final game – against Manchester United at Old Trafford – as Taylor helped to earn Bolton a 1–1 draw. The goal against United instantly gave Taylor cult hero status amongst the Bolton faithful. He then returned to West Bromwich Albion, playing in a further nine games and scoring twice, before re-joining Bolton Wanderers for a second loan spell, this time for the remainder of the 1997–98 season. During this period he scored two goals in eight games for Bolton, who were relegated from the Premier League on goal difference.