| Middlesbrough FC v Birmingham City FC 26/03/1988 | View match | |
| Middlesbrough FC v Sheffield United FC 02/04/1988 | View match | |
| Hull City FC v Middlesbrough FC 04/04/1988 | View match | |
| 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 |