| Leyton Orient FC v West Ham United FC 29/03/1999 | View match | |
| Aston Villa FC v West Ham United FC 02/04/1999 | £5.50 | |
| West Ham United FC v Charlton Athletic FC 05/04/1999 | £6.00 | |
| Leicester City FC v West Ham United FC 10/04/1999 | £3.50 | |
| West Ham United FC v Derby County FC 17/04/1999 | £5.00 | |
| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £4.50 | |
| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £4.00 | |
| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £2.00 | |
| West Ham United FC v Leeds United FC 01/05/1999 | £6.00 | |
| Dagenham & Redbridge v West Ham United FC 04/05/1999 | View match | |
| Everton FC v West Ham United FC 08/05/1999 | £5.50 | |
| West Ham United FC v Middlesbrough FC 16/05/1999 | £5.00 |