| Skonto Riga v Chelsea FC 25/08/1999 | £6.00 | |
| 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 | £5.00 | |
| Chelsea FC v AC Milan 15/09/1999 | £2.00 | |
| Chelsea FC v AC Milan 15/09/1999 | £4.00 | |
| Watford FC v Chelsea FC 18/09/1999 | £4.50 | |
| 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 |