The following season, Holland captained the club to a 5th-placed finish in the 2000–01 Premier League season, Ipswich's highest Premier League finish. He scored his first Premier League goal on 11 November in a 2–0 home win over Charlton Athletic at Portman Road. He also scored in League Cup wins over Millwall and Manchester City as Ipswich reached the semi-finals of the 2000–01 League Cup, losing 4–2 on aggregate to Birmingham City over two legs having won the first leg 1–0. Holland again started every league game that season, making 47 appearances in all competitions and scoring 5 goals. As a result of finishing 5th in the Premier League, Ipswich qualified for the UEFA Cup for the first time since the 1982–83 season.