 During his time at Cork City, Bennett played in The UEFA Cup and Champions league and also won a FAI Youth Cup medal in 2000, National league Medal in 2005 and 3 Munster Senior Cup medals.Following several bids, Bennett joined Reading on a two and a half-year contract for an undisclosed fee thought to be £250,000 on 30 January 2007.On 31 July 2007, he was loaned for six months to Southampton and made his debut during a home defeat to Crystal Palace.