Middlesbrough v Chelsea, 25 May 1988
| Score | 2-0 to Middlesbrough |
| Referee | Keith Hackett |
| Competition | League Division One and Two Play-Offs Final 1st leg |
| Venue | Ayresome Park, Middlesbrough |
| Attendance | 25,531 |
View Middlesbrough v Chelsea head to head
Goals:
| Trevor Senior | 30 |
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| Bernie Slaven | 81 |
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Starting lineup:
Goalkeeper
Stephen Pears
Defender/Right back
Gary Parkinson
Defender
Dean Glover
Defender
Gary Pallister
Defender/Centre back
Colin Cooper
Defender/Centre back
Tony Mowbray
Midfielder
Gary Hamilton
Midfielder
Paul Kerr
Midfielder
Stuart Ripley
Forward
Trevor Senior
Forward
Bernie Slaven
0 Chelsea
Goals:
Starting lineup:
Kevin Hitchcock
Goalkeeper
Steve Clarke
Defender
Colin Pates
Defender
Steve Wicks
Defender/Centre back
Clive Wilson
Defender/Midfielder
Tony Dorigo
Defender/Left back
John Bumstead
Midfielder
Joe McLaughlin
Midfielder
Pat Nevin
Midfielder/Forward
Kerry Dixon
Forward
Gordon Durie
Forward