| 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 | |
| West Ham United FC v Middlesbrough FC 18/11/1989 | £5.50 | |
| Blackburn Rovers FC v Middlesbrough FC 21/11/1989 | View match | |
| Middlesbrough FC v Oxford United FC 25/11/1989 | View match | |
| Middlesbrough FC v Port Vale FC 28/11/1989 | View match |