| Middlesbrough FC v Wimbledon 17/09/1988 | View match | |
| Tottenham Hotspur FC v Middlesbrough FC 24/09/1988 | £5.00 | |
| Middlesbrough FC v Tranmere Rovers FC 28/09/1988 | View match | |
| Coventry City FC v Middlesbrough FC 01/10/1988 | View match | |
| Middlesbrough FC v West Ham United FC 08/10/1988 | View match | |
| Tranmere Rovers FC v Middlesbrough FC 11/10/1988 | View match | |
| Middlesbrough FC v Luton Town FC 22/10/1988 | View match | |
| Newcastle United FC v Middlesbrough FC 26/10/1988 | View match | |
| Middlesbrough FC v Millwall FC 29/10/1988 | View match | |
| Liverpool FC v Middlesbrough FC 05/11/1988 | View match | |
| Middlesbrough FC v Queens Park Rangers FC 12/11/1988 | View match | |
| Arsenal FC v Middlesbrough FC 19/11/1988 | £5.50 |