He started his career with Aston Villa, also playing on loan at Torquay United and Port Vale. Following a season with Burnley, he signed with Rotherham United in 2000. He is considered something of a cult hero at the club, after helping the "Millers" to win promotion out of the Second Division in 2000–01. He was then bought by Cardiff City, and made almost 100 appearances for the Welsh side between 2003 and 2006. Then purchased by Ipswich Town, he made over 100 appearances for the club before earning a big money move to Crystal Palace. After returning from a loan spell at Norwich City, he wrote himself into the club's folklore by scoring in the final game of the 2009–10 season against Sheffield Wednesday, saving the Eagles from relegation and ultimately administration. Following these heroics he moved on to Huddersfield Town, and helped the "Terriers" to win promotion out of League One in 2012. He announced his retirement in 2014, having spent his final season as a player-coach at Ipswich Town.