| Chelsea FC v Sunderland FC 07/08/1999 | £3.00 | |
| Manchester City FC v Wolverhampton Wanderers FC 08/08/1999 | £7.50 | |
| Derby County FC v Arsenal FC 10/08/1999 | £3.50 | |
| West Ham United FC v Metz 10/08/1999 | £8.50 | |
| Bury FC v Notts County FC 10/08/1999 | £5.00 | |
| Manchester City FC v Burnley FC 11/08/1999 | £6.00 | |
| Chelsea FC v Skonto Riga 11/08/1999 | £5.00 | |
| Chelsea FC v Skonto Riga 11/08/1999 | £3.00 | |
| 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 | £5.00 | |
| Southampton FC v Leeds United FC 11/08/1999 | £3.50 |