| Everton FC v West Ham United FC 19/09/1999 | View match | |
| Coventry City FC v West Ham United FC 25/09/1999 | View match | |
| Osijek v West Ham United FC 30/09/1999 | View match | |
| West Ham United FC v Arsenal FC 03/10/1999 | View match | |
| West Ham United FC v AFC Bournemouth 13/10/1999 | View match | |
| Middlesbrough FC v West Ham United FC 17/10/1999 | View match | |
| Steaua Bucharest v West Ham United FC 21/10/1999 | View match | |
| West Ham United FC v Sunderland FC 24/10/1999 | View match | |
| Liverpool FC v West Ham United FC 27/10/1999 | £4.00 | |
| Leeds United FC v West Ham United FC 30/10/1999 | View match | |
| West Ham United FC v Steaua Bucharest 04/11/1999 | View match | |
| Chelsea FC v West Ham United FC 07/11/1999 | £3.50 |