| 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 | |
| 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 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £3.00 | |
| Chelsea FC v Arsenal FC 23/10/1999 | £2.50 | |
| Derby County FC v Chelsea FC 30/10/1999 | £6.50 | |
| Chelsea FC v Hertha BSC Berlin 03/11/1999 | £3.00 |