| Brighton & Hove Albion FC v Middlesbrough FC 18/01/1986 | £4.00 | |
| Fulham FC v Middlesbrough FC 27/09/1986 | £4.00 | |
| Bury FC v Middlesbrough FC 24/01/1987 | £6.50 | |
| Aston Villa FC v Middlesbrough FC 08/09/1987 | £4.00 | |
| Shrewsbury Town FC v Middlesbrough FC 19/03/1988 | £4.50 | |
| Middlesbrough FC v Manchester City FC 09/04/1988 | £7.50 | |
| Chelsea FC v Middlesbrough FC 28/05/1988 | £5.50 | |
| Manchester United FC v Middlesbrough FC 10/09/1988 | £3.50 | |
| 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 |