 Holroyd left Crewe after he was not offered a professional contract entering his third year of scholarship and joined Chester City, signing professional terms in 2006 after scoring 21 goals in 28 stats for Chester's youth team in the Football League Youth Alliance.He made his first-team debut for Chester at the start of the 2006–07 season, coming on as a 75th-minute substitute in Chester's 2–1 home defeat to Wrexham.The following season, Holroyd scored his first goal for Chester in a competitive match in October 2007, scoring a consolation goal in a 4–2 Football League Trophy defeat at Carlisle United.