A player long tracked by Spurs finally arrived in January 2005 in a joint £8 million deal with defender Michael Dawson from Nottingham Forest.
Started his career in the Republic of Ireland with Templeogue United, Lourdes Celtic and Cherry Orchard, from where he joined Nottingham Forest, preferring them over Arsenal and Manchester United, who he had trained with, but felt that Forest made him feel more wanted.
Had an impressive start to his Forest career with a goal on debut and showed that his tricky wing-play could be productive, as well as scoring goals himself with good skill from dead ball situations and possessing a powerful shot. Despite being a regular scorer and topping the club's goal-scorers for 2003-04, in August 2004 he handed in a transfer request saying that he could not stay at the club. However, he did not move on until January 2005, when Tottenham signed the little wide-man.
Despite being the one that had constantly been linked with Tottenham in the press, he did not live up to expectations when he played, but was hit by a series of injuries which limited his playing time with the club before Martin Jol decided that he was not the man to fill the left wing slot. Although his trickery had impressed in the Championship, his ability to go past a man was rarely displayed in a Lilywhite shirt and one goal was scant return, when he had been known for regularly hitting the target at Forest and with the Republic of Ireland.
While he may have been unlucky with injury and reports from within the club claimed he was one of the fittest in the team, his portly figure did not endear him to sections of the Spurs support, with doubts cast about his ability to stay in trim. His fine delivery with his left foot was sorely missed during his appearances with Spurs and at a time when he could have made the slot his own, it was a missed opportunity to make himself a regular in the side.
With his performances not shining through, he was allowed to join Charlton Athletic for a fee that could rise to £3,000,000 in August 2006. With Charlton being relegated, he missed much of the season that they went down, although there were high hopes he could have a beneficial effect on the Addicks fortunes if he could stay fit for their Championship campaign.
His fitness hampered his prolonged presence in the Charlton side, even though he took the captain's armband on occasion, with a £4 million transfer away from the club to Sunderland in the January transfer window seeing him join the Irish ranks at the Stadium of Light. Initially had a good spell at the club, but fell out of contention for a first team place as Steve Bruce made more high profile signings, leaving him to go out on loan at Sheffield United at the end of October 2010.
Was allowed to join Blackpool on a free transfer in January 2011, but made only two starts and three sub appearances, as the Seasiders were relegated at the end of the season, when he was released to find a new club.