After an impressive loan season from Chester City, Hessey signed a permanent deal with Maccesfield in May 2008
On loan from Chester City during the 2007/08 season, Hessey showed what he can offer in the team’s central defence as he battled to help keep Macclesfield in League Two. Committed and passionate, fiery but intelligent, Hessey lead the way on the pitch and, on more than one occasion as captain, made his presence felt in the dressing room as the Silkmen fought to secure their league status.
After making 26 appearances for the club during his season on loan, Hessey signed on permanently at the Moss Rose after his release from Chester in May 2008.