| Oldham Athletic FC v Chelsea FC 02/01/1999 | £5.50 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £3.50 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £3.50 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £1.00 | |
| Chelsea FC v Coventry City FC 16/01/1999 | £4.00 | |
| Arsenal FC v Chelsea FC 31/01/1999 | £4.00 | |
| Arsenal FC v Chelsea FC 31/01/1999 | £3.00 | |
| Arsenal FC v Chelsea FC 31/01/1999 | £5.00 | |
| Arsenal FC v Chelsea FC 31/01/1999 | £5.00 | |
| Chelsea FC v Oxford United FC 03/02/1999 | £3.00 | |
| Chelsea FC v Oxford United FC 03/02/1999 | £4.00 | |
| Chelsea FC v Oxford United FC 03/02/1999 | £4.50 |