| Tottenham Hotspur FC v Middlesbrough FC 24/09/1988 | £5.00 | |
| Middlesbrough FC v Charlton Athletic FC 17/12/1988 | £4.50 | |
| Middlesbrough FC v Manchester United FC 02/01/1989 | £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 | |
| Aston Villa FC v Middlesbrough FC 29/04/1989 | £5.00 | |
| Sheffield Wednesday FC v Middlesbrough FC 13/05/1989 | £2.50 | |
| Chelsea FC v Middlesbrough FC 25/03/1990 | £8.50 | |
| Brighton & Hove Albion FC v Middlesbrough FC 27/10/1990 | £2.00 | |
| Aston Villa FC v Middlesbrough FC 28/11/1990 | £5.00 | |
| Charlton Athletic FC v Middlesbrough FC 23/02/1991 | £4.00 |