Barry, a native of Ennis in County Clare, began his league career with UCD in 1996. He made 159 league appearances with the Students in his six years with the club and was snapped up by Shamrock Rovers in 2003.
Controversy followed later that year when Barry tested positive for cocaine and a nine month ban ensued, after which Barry returned to league football with Dublin City. But when the 'Vikings' folded in July 2006 Barry moved on to enjoy a successful stint with St Patrick's Athletic
Barry was released at the end of the 2008 season and in January 2009 he signed for Galway United, Gary Rogers moving in the opposite direction.
Barry spent two seasons at Terryland Park before signing for Pat Scully at Limerick FC in January 2011. When Barry arrived at Jackman Park his brother, Dave, was the first choice 'keeper, but an injury allowed Barry to claim the goalkeeper's gloves for himself and he went on to make 29 league appearances in his debut season with the club. In 2012 Barry made another 17 league appearances as Limerick took the First Division title and earned promotion back to the top flight.