Following an incident near a Leeds nightclub in January 2000, in which an Asian student suffered severe injuries, Bowyer and teammate Jonathan Woodgate were charged with causing grievous bodily harm with intent and affray. An initial trial collapsed in April 2001 after an article in a Sunday newspaper, and following a second trial, which ended in December 2001, Bowyer was cleared of both charges while Woodgate was convicted of affray and sentenced to community service. Bowyer was generally recognised as playing some of the finest football of his career during this period and would often go straight from court to play for Leeds. In 2005, the player agreed a £170,000 out-of-court settlement of a civil action for damages brought by the victim and his brother, who had been less seriously hurt in the assault.