Port Vale 1 Middlesbrough 3
Outcome: Won
Date: 11/29/1989
Manager: Bruce Rioch
Attendance: 6691
Competition: ZDSCup FirstRound
Played at: Ayresome Park
Goals:
| Goals | Time | Assists | |
| Bernie Slaven | |||
| Bernie Slaven | |||
| Simon Coleman | |||
Team
| Player | Yellow | Red | Subbed |
| Bernie Slaven | |||
| Stuart Ripley | |||
| Peter Davenport | |||
| Mark Procter | |||
| Trevor Putney | |||
| Mark Brennan | |||
| Colin Cooper | |||
| Nicky Mohan | |||
| Tony Mowbray | |||
| Simon Coleman | |||
| Kevin Poole |
Subs
| Player | Yellow | Red | Subbed |
| Mark Burke |