Ipswich continued to challenge for promotion during the 1999–2000 season. Holland kept up his impressive record of playing every game over the course of the season. He scored 10 goals in the league as Ipswich once again finished 3rd in the First Division, narrowly missing out on an automatic promotion place on the final day of the season. This meant Ipswich had qualified for the play-offs for the fourth season in a row. Holland started both legs of the semi-finals. The first leg of the semi-finals saw Ipswich come from 0–2 down to draw 2–2 away at Bolton, with Marcus Stewart scoring a brace. Ipswich won the second leg 5–3 at Portman Road, in a match that also saw two Bolton Wanderers players red carded, with goals from Jamie Clapham, Martijn Reuser and a Jim Magilton Hat-trick. Ipswich progressed to the play-offs final following a 7–5 aggeregate win over Bolton Wanderers. Holland started in and captained Ipswich in the final on 29 May 2000 against Barnsley at Wembley Stadium. Ipswich again came from behind to eventually win the final 4–2, following goals from Tony Mowbray, Richard Naylor, Marcus Stewart and Martijn Reuser, winning promotion to the Premier League following a 5-year absence from the top flight.