| Middlesbrough FC v Manchester City FC 09/04/1988 | £7.50 | |
| Ipswich Town FC v Middlesbrough FC 23/04/1988 | View match | |
| Middlesbrough FC v Plymouth Argyle FC 30/04/1988 | View match | |
| Barnsley FC v Middlesbrough FC 02/05/1988 | View match | |
| Middlesbrough FC v Leicester City FC 07/05/1988 | View match | |
| Bradford City FC v Middlesbrough FC 15/05/1988 | View match | |
| Middlesbrough FC v Bradford City FC 18/05/1988 | View match | |
| Middlesbrough FC v Chelsea FC 25/05/1988 | View match | |
| Chelsea FC v Middlesbrough FC 28/05/1988 | £5.50 | |
| Derby County FC v Middlesbrough FC 27/08/1988 | View match | |
| Middlesbrough FC v Norwich City FC 03/09/1988 | View match | |
| Manchester United FC v Middlesbrough FC 10/09/1988 | £3.50 |