The 2002–03 season saw Ryan in tremendous form and he capped it off by scoring the goal that won the 2002–03 league title for Bohemians in the dying minutes of a 1–0 win over Shelbourne at Tolka Park on 12 January 2003.
Ryan then won the League of Ireland championship with Shelbourne in 2006, but the squad broke up due to financial problems.
Ryan then joined Scottish First Division club Dunfermline Athletic in January 2007.
In January 2008, having failed to make much impact at Dunfermline, Ryan moved back to Ireland to play for St Patrick's Athletic as new Dunfermline manager Jim McIntyre began reshaping the club's squad.
[3][4] 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.