| Aston Villa FC v Middlesbrough FC 30/01/1990 | View match | |
| Middlesbrough FC v Portsmouth FC 03/02/1990 | View match | |
| Middlesbrough FC v Aston Villa FC 06/02/1990 | View match | |
| AFC Bournemouth v Middlesbrough FC 10/02/1990 | View match | |
| Oxford United FC v Middlesbrough FC 24/02/1990 | View match | |
| Brighton & Hove Albion FC v Middlesbrough FC 28/02/1990 | £3.50 | |
| Middlesbrough FC v West Ham United FC 03/03/1990 | View match | |
| Middlesbrough FC v Watford FC 07/03/1990 | View match | |
| Hull City FC v Middlesbrough FC 10/03/1990 | View match | |
| Middlesbrough FC v Blackburn Rovers FC 17/03/1990 | View match | |
| Plymouth Argyle FC v Middlesbrough FC 20/03/1990 | View match | |
| Chelsea FC v Middlesbrough FC 25/03/1990 | £8.50 |