| 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 | |
| West Ham United FC v Middlesbrough FC 18/11/1989 | £6.00 | |
| Brighton & Hove Albion FC v Middlesbrough FC 28/02/1990 | £3.50 | |
| Chelsea FC v Middlesbrough FC 25/03/1990 | £8.50 | |
| Brighton & Hove Albion FC v Middlesbrough FC 27/10/1990 | £4.00 | |
| Brighton & Hove Albion FC v Middlesbrough FC 27/10/1990 | £3.50 | |
| Aston Villa FC v Middlesbrough FC 28/11/1990 | £5.00 | |
| Manchester City FC v Middlesbrough FC 19/12/1990 | £9.50 | |
| Charlton Athletic FC v Middlesbrough FC 23/02/1991 | £4.00 | |
| Brighton & Hove Albion FC v Middlesbrough FC 09/11/1991 | £3.50 |