In the summer of 1997, Holland joined Ipswich Town for a fee of £800,000. He made his debut for Ipswich on the opening day of the 1997–98 season, starting in a 0–0 draw with Queens Park Rangers. He scored his first goal for the club on 20 September 1997, netting in a 2–3 loss to Stoke City. Holland became an integral part of the side during his first season at Portman Road, starting every league and cup game as Ipswich finished 5th in the First Division, qualifying for the First Division play-offs as a result. Ipswich lost out 0–2 on aggregate over two legs to Charlton Athletic in the play-offs semi-finals. In total Holland made 59 appearances in all competitions during his first season at the club, scoring 12 goals, including a brace in a 0–3 away win over Torquay United in a League Cup second round tie. He won the club's Player of the Year award for the 1997–98 season.