| Tottenham Hotspur FC v Middlesbrough FC 24/09/1988 | £5.00 | |
| Arsenal FC v Middlesbrough FC 19/11/1988 | £5.50 | |
| Arsenal FC v Middlesbrough FC 19/11/1988 | £5.50 | |
| Middlesbrough FC v Charlton Athletic FC 17/12/1988 | £4.50 | |
| Middlesbrough FC v Manchester United FC 02/01/1989 | £4.00 | |
| Luton Town FC v Middlesbrough FC 18/02/1989 | £4.00 | |
| Charlton Athletic FC v Middlesbrough FC 01/04/1989 | £3.00 | |
| Charlton Athletic FC v Middlesbrough FC 01/04/1989 | £3.00 | |
| Queens Park Rangers FC v Middlesbrough FC 15/04/1989 | £1.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 13/05/1989 | £2.50 | |
| Middlesbrough FC v Brighton & Hove Albion FC 18/10/1989 | £4.50 | |
| Chelsea FC v Middlesbrough FC 25/03/1990 | £8.50 |