| 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 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £5.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| 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 | £3.50 | |
| Middlesbrough FC v West Ham United FC 12/12/1998 | £4.50 | |
| Manchester United FC v Middlesbrough FC 19/12/1998 | £6.50 |