The 2000 Football League First Division play-off final was an association football match played at Wembley Stadium on 29 May 2000, to determine the third and final team to gain promotion from the First Division to the Premiership in the 1999–2000 season. Ipswich Town faced Barnsley in the last domestic competitive fixture to be played at the original Wembley Stadium.

The match was both teams' first appearance in a First Division play-off final. It was the first time Barnsley had been in the play-offs, having been relegated to the First Division after the 1997–98 season, and finishing mid-table the following season. Ipswich made the play-offs for the fourth consecutive season, but this was the first time they had advanced further than the semifinals. Watched by a crowd of more than 73,000, Ipswich Town came from behind to win 4–2 and secured promotion to the Premiership.

Ipswich finished the regular 1999–2000 Football League season in third place in the First Division, the second tier of the English football league system, one place ahead of Barnsley. Both therefore missed out on the two automatic places for promotion to the Premiership and instead took part in the play-offs to determine the third promoted team. It was Ipswich's fourth year running in the playoffs. Ipswich finished two points behind Manchester City (who were promoted in second place) and four behind league winners Charlton Athletic. Barnsley were in fourth place in the league, a further five points behind Ipswich – they also finished as the highest scorers in the division with 88 goals.

On the final day of the league season Ipswich played Walsall, and won 2–0. At one point, after David Johnson scored his first goal, second place Manchester City were trailing to Blackburn, meaning that Ipswich would qualify for promotion automatically. However, City eventually scored four goals to win the match and secure promotion, meaning Ipswich needed to seek promotion through the play-offs.

In the play-off semi-finals, Ipswich faced sixth-placed Bolton Wanderers who had beaten them in the semifinal the previous year. After being 2–0 down in the first leg away at the Reebok Stadium, Marcus Stewart scored two to secure a 2–2 draw. In the second leg at Portman Road, Jim Magilton scored a hat-trick as Ipswich won 5–3, winning 7–5 on aggregate. Barnsley won the first leg 4–0 away against Birmingham City at St Andrew's. Despite losing the second leg 2–1 at Oakwell, they reached the final 5–2 on aggregate.

This was Ipswich's fourth consecutive appearance in the play-offs, and fifth in total. It was the first time they had progressed to the final, having lost in the play-off semifinals for the past three years, to Sheffield United in the 1997 play-offs, Charlton Athletic in the 1998 play-offs, and Bolton Wanderers in the 1999 play-offs. Ipswich's previous appearance at Wembley was in the 1978 FA Charity Shield against Nottingham Forest. It was Barnsley's first appearance in both the play-offs and at Wembley. During the regular season, Ipswich had beaten Barnsley 6–1 at Portman Road and 2–0 at Oakwell, and Ipswich striker Marcus Stewart stated before the game that he would have "picked Barnsley ... perhaps they'll be thinking we're their bogey side". Barnsley had played 55 games during the regular season and scored 106 goals, with Craig Hignett (20 goals), Neil Shipperley (15), Darren Barnard (15) and Mike Sheron (11) all in double figures for goals scored. Ipswich were going into the match without their fan's and player's player of the season: James Scowcroft was out with a hamstring injury. Dutchman Martijn Reuser was slated to replace him in the starting line-up, and John McGreal came back into the team following an ankle injury.

The play-off final was the last domestic competitive fixture to be played at the original Wembley Stadium. Match referee Terry Heilbron became the first person to officiate in four play-off finals, with the 2000 final being his second consecutive final, and his last before retirement. Promotion from the First Division to the Premiership was estimated to be worth up to £12 million.

Ipswich kicked off and immediately sought to press Barnsley, with David Johnson making a heavy challenge on goalkeeper Kevin Miller but injuring himself in the process. After just five minutes, an own goal from Ipswich's goalkeeper Richard Wright put the Yorkshire club ahead: a Craig Hignett strike from 32 yards (29 m) rebounded off the bar, hit Wright on the arm and was deflected into the net. Ipswich's first shot came on nine minutes from Mark Venus and gradually the East Anglian side regained confidence. The teams exchanged challenges and chances until, in the twenty-second minute of the game, Johnson, who had picked up a shoulder injury after challenging the goalkeeper in the early stages of the match, was replaced by substitute Richard Naylor. Barnsley's Hignett struck a shot in the 25th minute which passed narrowly outside the post with opposition goalkeeper Wright beaten, and two minutes later a shot from Ipswich's Matt Holland was blocked for a corner. Played to the far post by Jim Magilton, the ball was headed past Miller by Ipswich's 36-year-old defender Tony Mowbray to level the score. The goal sparked a period of Ipswich dominance with attempts from Holland and Naylor being saved by Miller. One minute before half-time, Richard Wright's challenge on Hignett was deemed a penalty: Darren Barnard stepped up to take the kick which Wright saved to his right and the half ended 1–1.