| Chelsea FC v AC Milan 15/09/1999 | £5.00 | |
| Chelsea FC v AC Milan 15/09/1999 | £4.00 | |
| Watford FC v Chelsea FC 18/09/1999 | £4.50 | |
| Hertha BSC Berlin v Chelsea FC 21/09/1999 | View match | |
| Middlesbrough FC v Chelsea FC 25/09/1999 | View match | |
| Chelsea FC v Galatasaray SK 28/09/1999 | £3.00 | |
| Chelsea FC v Galatasaray SK 28/09/1999 | £4.00 | |
| Chelsea FC v Galatasaray SK 28/09/1999 | £3.00 | |
| Chelsea FC v Manchester United FC 03/10/1999 | £5.00 | |
| Chelsea FC v Manchester United FC 03/10/1999 | £5.50 | |
| Chelsea FC v Huddersfield Town FC 13/10/1999 | £3.50 | |
| Chelsea FC v Huddersfield Town FC 13/10/1999 | £4.50 |