| Aston Villa FC v West Ham United FC 16/08/1999 | £4.00 | |
| West Ham United FC v Leicester City FC 21/08/1999 | £5.00 | |
| Metz v West Ham United FC 24/08/1999 | View match | |
| Bradford City FC v West Ham United FC 28/08/1999 | £4.00 | |
| West Ham United FC v Watford FC 11/09/1999 | £5.00 | |
| West Ham United FC v Osijek 16/09/1999 | £5.00 | |
| Everton FC v West Ham United FC 19/09/1999 | £5.00 | |
| Coventry City FC v West Ham United FC 25/09/1999 | £5.00 | |
| Osijek v West Ham United FC 30/09/1999 | View match | |
| West Ham United FC v Arsenal FC 03/10/1999 | £6.00 | |
| West Ham United FC v AFC Bournemouth 13/10/1999 | View match | |
| Middlesbrough FC v West Ham United FC 17/10/1999 | £5.00 |