| Chelsea FC v Derby County FC 16/05/1999 | £3.00 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £4.00 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £1.30 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £3.00 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £3.50 | |
| Chelsea FC v Skonto Riga 11/08/1999 | £4.50 | |
| Chelsea FC v Skonto Riga 11/08/1999 | £3.00 | |
| Chelsea FC v Skonto Riga 11/08/1999 | £3.00 | |
| Chelsea FC v Skonto Riga 11/08/1999 | £5.00 | |
| 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 | £3.50 |