He signed for Everton as a trainee and when released signed up with Coventry City where he was a regular in the reserves. He joined Accrington Stanley in 2005, and was an ever-present for the first half of the 2005–06 season, making 26 Conference appearances as the side headed for promotion back to The Football League. In January 2006 he joined Yeovil Town. Barry made 64 league appearances for the Glovers, before being released in May 2008. This stint included an appearance at Wembley Stadium in the Football League One play–off final against Blackpool in 2006–07. He scored his only goal for Yeovil in a 2–1 defeat at Shrewsbury Town in the Football League Trophy on 31 October 2006. 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. His contract with Chester was terminated on 11 January 2010 with immediate notice. He signed for Wrexham on an 18-month deal on 16 January, but left the club less than one week later after asking to be released from his contract. On 24 January 2010 he signed for Conference North sideFleetwood Town, after being offered three times the amount he was paid with Wrexham. This move angered Wrexham's manager, Dean Saunders. He was named in the Conference Team of the Year for the 2010–11 season after Fleetwood reached the play-off semi-finals. It was announced on 7 May 2013, that Fleetwood would not be offering the midfielder a new contract, and would therefore be released. In May 2013, he joined Forest Green Rovers on a three-year deal. He made his debut for the club on 10 August 2013 in an 8–0 win against Hyde at The New Lawn. He scored his first goal for the club on 17 August 2013 in an away defeat against Lincoln City. On 8 October 2014, having failed to make an appearance in the 2014–15 season for Forest Green, he re-joined League Two club Accrington Stanley on a 93-day loan. In January 2015, the loan deal was extended until the end of the season. On 7 June 2016, Barry signed for National League side Wrexham. Barry was released by Wrexham at the end of the 2016–17 season.
