| Watford FC v Middlesbrough FC 30/09/1989 | View match | |
| Halifax Town A.F.C v Middlesbrough FC 03/10/1989 | View match | |
| Middlesbrough FC v Plymouth Argyle FC 14/10/1989 | View match | |
| Middlesbrough FC v Brighton & Hove Albion FC 18/10/1989 | £4.50 | |
| Oldham Athletic FC v Middlesbrough FC 21/10/1989 | View match | |
| Middlesbrough FC v Wimbledon 25/10/1989 | View match | |
| Middlesbrough FC v West Bromwich Albion FC 28/10/1989 | View match | |
| Port Vale FC v Middlesbrough FC 30/10/1989 | View match | |
| Newcastle United FC v Middlesbrough FC 04/11/1989 | View match | |
| Wimbledon v Middlesbrough FC 08/11/1989 | View match | |
| Middlesbrough FC v Swindon Town FC 11/11/1989 | View match | |
| West Ham United FC v Middlesbrough FC 18/11/1989 | £6.00 |