Hessey joined Chester after the club were promoted back to the Football League in 2004 and was a first-choice player for much of his first three years at the club, although he quite often missed games because of injury and suspension problems. The most notable was a five-match ban for violent conduct at the start of the 2006–07 season after an incident in the home game against Stockport County the previous season. Hessey has proved to be a versatile player, operating in both central defensive and full back roles and also in a holding midfield spot. He scored twice at Chester; once in a Football League Trophy tie against Rochdale and once in a league match against Rushden & Diamonds.
