| Arsenal FC v Chelsea FC 31/01/1999 | £3.00 | |
| 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 | |
| Chelsea FC v Southampton FC 06/02/1999 | £3.50 | |
| Chelsea FC v Southampton FC 06/02/1999 | £2.00 | |
| Chelsea FC v Southampton FC 06/02/1999 | £3.00 | |
| Sheffield Wednesday FC v Chelsea FC 13/02/1999 | £3.00 | |
| Chelsea FC v Blackburn Rovers FC 17/02/1999 | £3.00 | |
| Chelsea FC v Blackburn Rovers FC 17/02/1999 | £1.50 | |
| Nottingham Forest FC v Chelsea FC 20/02/1999 | £3.50 | |
| Chelsea FC v Liverpool FC 27/02/1999 | £4.50 |