on 7 February. He then made his competitive debut against Dungannon Swifts in the Setanta Cup on 26 February, scoring two goals. After numerous man of the match displays at Cork City, it was announced on 9 July that O'Callaghan, along with ex-teammate Bas Savage, had joined Tranmere Rovers on a two-year contract. However, on 13 February 2009, O'Callaghan had his contract cancelled by Tranmere Rovers after suffering illness and failing to settle at the club. Returning to his native Ireland, O'Callaghan signed for Dundalk in February 2009, scoring against Celtic on his debut. He left the club after just four months. In July 2009, English club Yeovil Town confirmed won O'Callaghan's signature. On 23 December 2009 it was announced that his contract would not be renewed, after seven starts and five substitute appearances in six months, leaving him without a club. He returned to Cork City for a third time under new boss Roddy Collins. After the departure of Dan Murray, he was named captain. O'Callaghan and the rest of the staff of the club became free agents after the winding up of the club in February 2010. He turned out for the club in a pre-season friendly at Crosshaven, but decided against playing for his local club due to the uncertainty surrounding their future. George signed for Waterford United on 8 April 2010. He made his debut in the away day defeat to Monaghan United. In his second game for the club he scored a 35-yard wonder goal against Tramore in the Munster Cup. He scored five goals in the "Blues" 9–0 victory over Tralee Dynamos in the League of Ireland Cup on 11 May 2010, becoming the first Waterford player to score five in a game since Alfie Hale. At the end of June 2010 George decided to return to Cork City to help the club's attempt to achieve promotion from the First Division. He made his debut on 23 July against Finn Harps. He left the club once again before the end of the year. In February 2011 he joined League One side Brentford on a two-week trial. He signed for Conference National club Cambridge United on non-contract terms in April 2011. However, he was never utilised by the club in his brief time there. In October 2011 he signed for DPMM FC, the only professional football club in Brunei. He had previously spent a brief