Initially being rejected by Arsenal for being “too small,” Holland joined Bournemouth, where he played a total of 104 games, scoring 18 goals and becoming captain. Holland joined Ipswich Town in 1997, and captained the team into the Premier League. He is best remembered at Ipswich for his consistency, having played 223 consecutive games. Holland moved to Charlton Athletic in 2003. He again became captain and was a very present figure in his first season. Holland went on to become one of the longest-serving Charlton players.