Career
Ryan had a schoolboy career with the Geraldines nursery club in Limerick and had progressed to play for Limerick and Galway United, before Stephen Kenny signed him for in January 2002. He made his debut for the club away to Cork City on 20 January. Ryan then joined Scottish First Division club Dunfermline Athletic in January 2007.
He made nine appearances in the 2007-2008 season before returning to Ireland in January 2008.
In January 2008, having failed to make much impact at Dunfermline, Ryan moved back to Ireland to play for Street Patrick"s Athletic as new Dunfermline manager Jim McIntyre began reshaping the club"s squad. In February 2010, Ryan signed for Galway United after spending most of pre-season there.
However, due to Galway"s desire to ease financial problems by releasing players, Ryan was able to sign for his hometown club of Limerick in the mid-season transfer window. He returned to Galway United in 2011 starting his third spell with the club
He joined Monaghan United for the 2012 season.
On 18 June 2012, the club announced their withdrawal from the League of Ireland and all of their playing staff were released by the club Bobby is currently coaching with Street.Mochta"s Football Club in Clonsilla, Dublin 15.