| Chelsea FC v Leeds United FC 05/05/1999 | £3.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £2.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £3.00 | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.00 | |
| Chelsea FC v Derby County FC 16/05/1999 | £3.50 | |
| Chelsea FC v Bologna 31/07/1999 | View match | |
| Chelsea FC v Sunderland FC 07/08/1999 | £3.50 | |
| 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 Skonto Riga 11/08/1999 | £3.00 |