| Chelsea FC v Middlesbrough FC 26/09/1998 | £1.00 | |
| 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 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Manchester United FC v Middlesbrough FC 19/12/1998 | £6.00 | |
| Manchester United FC v Middlesbrough FC 19/12/1998 | £4.50 | |
| Manchester United FC v Middlesbrough FC 03/01/1999 | £7.00 | |
| Liverpool FC v Middlesbrough FC 06/02/1999 | £5.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 20/02/1999 | £5.00 | |
| Middlesbrough FC v Charlton Athletic FC 10/04/1999 | £4.00 |