From TheChels.info - The Chelsea Football Club Wiki
The 1987-88 play-offs were a short-lived system whereby the club which finished fourth from bottom in the First Division was matched in a play-off competition with the teams which finished 3rd, 4th and 5th in the Second Division to decide the final promotion/relegation place. Having finished 18th in the First Division that season, Chelsea were forced to take part in the play-offs along with Blackburn Rovers, Middlesbrough and Bradford City. In the semi-finals Chelsea comfortably beat Blackburn 6-1 on aggregate, but were unable to overturn a 2-0 first leg deficit against Middlesbrough in the final and were thus relegated.
|1987-88||Sun||15||May||1988||Semi-final 1st leg||Blackburn Rovers||Away||Won||2-0|
|1987-88||Wed||18||May||1988||Semi-final 2nd leg||Blackburn Rovers||Home||Won||4-1||(6-1 aggregate)|
|1987-88||Wed||25||May||1988||Final 1st leg||Middlesbrough||Away||Lost||0-2|
|1987-88||Sat||28||May||1988||Final 2nd leg||Middlesbrough||Home||Won||1-0||(1-2 aggregate)|