On 19 June 2008, Barry signed a two-year contract with Chester City. He went on to feature in 43 of Chester's 46 league games during their relegation season from Football League Two, with his only goal being a spectacular long-range effort against Lincoln City in January 2009.
On June 19, 2008, Barry signed a two-year contract with Chester City. He played in 43 of their 46 league games during their relegation season from Football League Two, scoring his only goal against Lincoln City in January 2009.