| Chelsea FC v Middlesbrough FC 26/09/1998 | £1.00 | |
| Helsingborg v Chelsea FC 01/10/1998 | £24.00 | |
| Liverpool FC v Chelsea FC 04/10/1998 | £6.50 | |
| Chelsea FC v Charlton Athletic FC 17/10/1998 | £2.00 | |
| Chelsea FC v Charlton Athletic FC 17/10/1998 | £3.00 | |
| Chelsea FC v Charlton Athletic FC 17/10/1998 | £3.50 | |
| Chelsea FC v Charlton Athletic FC 17/10/1998 | £4.00 | |
| Chelsea FC v Charlton Athletic FC 17/10/1998 | £3.50 | |
| Chelsea FC v FC Copenhagen 22/10/1998 | £3.00 | |
| Leeds United FC v Chelsea FC 25/10/1998 | £4.50 | |
| Chelsea FC v Aston Villa FC 28/10/1998 | £4.50 | |
| Chelsea FC v Aston Villa FC 28/10/1998 | £2.00 |