| Aston Villa FC v Chelsea FC 21/03/1999 | £3.50 | |
| Charlton Athletic FC v Chelsea FC 03/04/1999 | £3.50 | |
| Charlton Athletic FC v Chelsea FC 03/04/1999 | £4.00 | |
| Chelsea FC v Real Mallorca/RCD Mallorca 08/04/1999 | £6.50 | |
| Chelsea FC v Real Mallorca/RCD Mallorca 08/04/1999 | £8.00 | |
| Chelsea FC v Real Mallorca/RCD Mallorca 08/04/1999 | £3.00 | |
| Chelsea FC v Real Mallorca/RCD Mallorca 08/04/1999 | £3.00 | |
| Chelsea FC v Real Mallorca/RCD Mallorca 08/04/1999 | £8.50 | |
| Wimbledon v Chelsea FC 11/04/1999 | £4.50 | |
| Middlesbrough FC v Chelsea FC 14/04/1999 | £3.50 | |
| Chelsea FC v Leicester City FC 18/04/1999 | £3.50 | |
| Chelsea FC v Leicester City FC 18/04/1999 | £4.00 |