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O'Callaghan was appointed as manager of Sabah in the Malaysia Premier League in 2014. He was sacked in January 2015, along with Singapore international Fazrul Nawaz, after the pair began missing training sessions.

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 period at the club between his time at Port Vale and Cork City. He had decided to leave both the club and the country as his family were not enjoying life in the Far East. O'Callaghan signed for Dover Athletic of the Conference South in September 2012.

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.

In January 2008 he decided to terminate his contract with Ipswich, having played seventeen games for the club, manager Jim Magilton explained: "George is a great lad but he's 28 now and needs to be playing regular first-team football. We have not been able to give him that here and we won't stand in his way of moving on now." On 31 January 2008, O'Callaghan returned home to Cork City, signing a three-year deal under new manager Alan Mathews. O'Callaghan made his debut in a friendly against Shelbourne on 7 February. He then made his competitive debut against Dungannon Swifts in the Setanta Cup on 26 February, scoring two goals.

In July 2006 he was given time off due to a falling out between himself and manager Damien Richardson. In September 2006, O'Callaghan joined English club Ipswich Town on trial with a view to a permanent deal. He remained training at Ipswich for the following two months, unable to formally sign because of UEFA's transfer window system. In January 2007, the clubs finally negotiated a deal despite strong words on both sides, concluding in an undisclosed fee (speculated to be around £60,000) which saw him sign an eighteen-month contract with Ipswich. On his full Ipswich debut he was sent off playing in the FA Cup against Watford, after an alleged stamp on defender Danny Shittu. However O'Callaghan was to escape a further three match ban after a successful appeal. On 7 May 2007, O'Callaghan scored his first goal for the "Tractor Boys" in the 5–1 win over Barnsley.

In August 2007, Ipswich agreed terms with Brighton & Hove Albion to sell O'Callaghan for around £85,000, rising to £105,000 based on appearances, although this transfer fell through as the club and player were unable to reach an agreement on personal terms. He did however move to Withdean on loan until the end of December 2007. He rejected the chance to sign permanently at Brighton, stating that chairman Dick Knight was being unrealistic with the wages he was offering both himself and fellow striker Bas Savage. Both players left the club at the end of December 2007.

In 2005, Cork City picked up their first league title in twelve years and O'Callaghan picked up a winners medal. He scored eleven goals in all competitions, including in the 2005–06 UEFA Cup, and was also announced as the eircom League Player of the Year for 2005. He also played in the 2005 FAI Cup Final defeat to Drogheda United at Lansdowne Road. He also was named as League of Ireland Player of the Year.

O'Callaghan drove through a red light in Cork at 2:40am on 13 October 2004, and upon his arrest admitted that he had "had seven or eight pints, a few shots and a few cocktails". It took three years before his case went to court, at which point the court handed him a €300 fine and gave him a two-year driving ban; he stated that "I have learned from my mistake". He is the cousin of the internationally capped Irish Rugby union lock Donncha O'Callaghan.

He returned home to Cork in 2002 after his contract ended at Port Vale. Shortly after, he signed for his hometown club Cork City making his debut in the opening game of the 2002–03 season against Shelbourne in 3–0 home win in which he scored. He went on to form a useful striking partnership with John O'Flynn. Following the arrival of Neale Fenn in 2004, O'Callaghan was moved to midfield by then manager Pat Dolan, to accommodate the new player.

O'Callaghan went on trial with Port Vale at the age of fifteen, and was signed up almost immediately. After two years, he was offered a professional contract. After being named the club's Young Player of the Year, O'Callaghan was on the point of breaking into the first team in the 1998–99 season, until John Rudge was sacked. Brian Horton took over as manager and O'Callaghan was put back into the youth squad. Thirteen months later he made a return to the senior squad, scoring in a draw with Crewe Alexandra. He stayed in the side for the rest of the season and signed a new two-year deal with the club despite an offer from Tottenham Hotspur. Port Vale were relegated to the Second Division that year. O'Callaghan was top-scorer seven games into the 2000–01 season but was suddenly dropped after a 3–0 loss to Cardiff City. It would be his last game for the "Valiants".

O'Callaghan started his career with Port Vale in 1995, he made 41 appearances for the club before joining Cork City in 2002. He spent five years at his home town club, making 150 league appearances. This was followed by a return to English football with Ipswich Town, before a brief return to Cork in 2008. In the summer of 2008 he signed with Tranmere Rovers, before brief spells with Dundalk and Yeovil Town in 2009. He then returned to his homeland for short stays at Waterford United and former club Cork City. He was briefly with Cambridge United in 2011, before he emigrated to Brunei to briefly play for DPMM FC. He joined Dover Athletic for a brief stay in September 2012. He began his management career with Malaysian side Sabah in 2014, but lasted only months in the role.

George Paul O'Callaghan (born 5 September 1979) is an Irish former football player and manager.