| Chelsea FC v Skonto Riga 11/08/1999 | £5.00 | |
| Leicester City FC v Chelsea FC 14/08/1999 | £3.50 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £3.00 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £3.50 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £4.00 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £2.50 | |
| Skonto Riga v Chelsea FC 25/08/1999 | £6.00 | |
| Wimbledon v Chelsea FC 28/08/1999 | View match | |
| Chelsea FC v Newcastle United FC 11/09/1999 | £3.00 | |
| Chelsea FC v Newcastle United FC 11/09/1999 | £3.50 | |
| Chelsea FC v AC Milan 15/09/1999 | £4.00 | |
| Chelsea FC v AC Milan 15/09/1999 | £2.00 |