| Chelsea FC v Middlesbrough FC 17/05/1997 | £11.50 | |
| Manchester City FC v Middlesbrough FC 20/12/1997 | £4.50 | |
| Aston Villa FC v Middlesbrough FC 23/08/1998 | £4.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 13/09/1998 | £4.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 13/09/1998 | £2.00 | |
| Chelsea FC v Middlesbrough FC 26/09/1998 | £1.00 | |
| Southampton FC v Middlesbrough FC 07/11/1998 | £5.50 | |
| Charlton Athletic FC v Middlesbrough FC 14/11/1998 | £4.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.50 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £5.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 |