| Aston Villa FC v West Ham United FC 16/08/1999 | £2.50 | |
| 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 | |
| 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 | |
| West Ham United FC v Arsenal FC 03/10/1999 | £6.00 | |
| Middlesbrough FC v West Ham United FC 17/10/1999 | £5.00 | |
| West Ham United FC v Sunderland FC 24/10/1999 | £5.00 | |
| Liverpool FC v West Ham United FC 27/10/1999 | £4.50 |