| West Ham United FC v Tottenham Hotspur FC 07/08/1999 | £5.00 | |
| Queens Park Rangers FC v Huddersfield Town FC 07/08/1999 | £5.00 | |
| Bury FC v Gillingham FC 07/08/1999 | £6.00 | |
| Coventry City FC v Southampton FC 07/08/1999 | £3.50 | |
| 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 | |
| Charlton Athletic FC v Barnsley FC 07/08/1999 | £5.50 | |
| Arsenal FC v Leicester City FC 07/08/1999 | £1.50 | |
| Manchester City FC v Wolverhampton Wanderers FC 08/08/1999 | £7.50 | |
| Derby County FC v Arsenal FC 10/08/1999 | £3.50 |