The 1988 Football League Second Division play-off Final was an association football match contested between Chelsea and Middlesbrough over two legs on 25 May 1988 and 28 May 1988. It was to determine which club would play the next season in the First Division, the top tier of English football. Chelsea had finished the season fourth from bottom in the First Division, while Middlesbrough were third in the Second Division. They were joined in the play-offs by the teams that had finished fourth and fifth in the Second Division: Chelsea defeated Blackburn Rovers in their play-off semi-final, while Middlesbrough beat Bradford City.