Middlesbrough 2 Portsmouth 1
Outcome: Won
Date: 12/21/1988
Manager: Bruce Rioch
Attendance: 6853
Competition: Second Round
Played at: Ayresome Park
Goals:
| Goals | Time | Assists | |
| Bernie Slaven | |||
| Dean Glover | |||
Team
| Player | Yellow | Red | Subbed |
| Stephen Pears | |||
| Colin Cooper | |||
| Gary Pallister | |||
| Gary Parkinson | |||
| Tony Mowbray | |||
| Dean Glover | |||
| Mark Brennan | |||
| Gary Hamilton | |||
| Bernie Slaven | |||
| Stuart Ripley | |||
| Peter Davenport |
Subs
| Player | Yellow | Red | Subbed |
| Paul Kerr |