Born in Leicester, Heskey started his career with Leicester City after progressing through their youth system, making his first-team debut in 1995. After winning the League Cup in 1997 and 2000 he made an £11 million move to Liverpool in 2000, which, at the time, was the record transfer fee paid by the club. At Liverpool, he won multiple honours, including the FA Cup in 2001. He moved to Birmingham City in 2004 and after their relegation from the Premier League signed for Wigan Athletic for a club record £5.5 million fee in 2006. He signed for Aston Villa in 2009 and was released in 2012 before signing for A-League club Newcastle Jets. After two years, he returned to England, finishing his career with Championship club Bolton Wanderers.