| Chelsea FC v Huddersfield Town FC 13/10/1999 | £3.50 | |
| Chelsea FC v Huddersfield Town FC 13/10/1999 | £4.50 | |
| Liverpool FC v Chelsea FC 16/10/1999 | View match | |
| Galatasaray SK v Chelsea FC 20/10/1999 | View match | |
| Chelsea FC v Arsenal FC 23/10/1999 | £2.50 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £3.00 | |
| AC Milan v Chelsea FC 26/10/1999 | View match | |
| Derby County FC v Chelsea FC 30/10/1999 | £6.50 | |
| Chelsea FC v Hertha BSC Berlin 03/11/1999 | £3.00 | |
| Chelsea FC v Hertha BSC Berlin 03/11/1999 | £4.50 | |
| Chelsea FC v Hertha BSC Berlin 03/11/1999 | £5.00 | |
| Chelsea FC v Hertha BSC Berlin 03/11/1999 | £5.00 |