| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £2.00 | |
| West Ham United FC v Leeds United FC 01/05/1999 | View match | |
| Dagenham & Redbridge v West Ham United FC 04/05/1999 | View match | |
| Everton FC v West Ham United FC 08/05/1999 | View match | |
| West Ham United FC v Middlesbrough FC 16/05/1999 | View match | |
| Jokerit v West Ham United FC 24/07/1999 | View match | |
| West Ham United FC v SC Heerenveen 28/07/1999 | View match | |
| Charlton Athletic FC v West Ham United FC 30/07/1999 | £6.00 | |
| SC Heerenveen v West Ham United FC 04/08/1999 | View match | |
| West Ham United FC v Tottenham Hotspur FC 07/08/1999 | £5.50 | |
| West Ham United FC v Metz 10/08/1999 | View match | |
| Aston Villa FC v West Ham United FC 16/08/1999 | £3.50 |