| West Ham United FC v Middlesbrough FC 16/05/1999 | £5.00 | |
| West Ham United FC v Jokerit 17/07/1999 | £6.00 | |
| West Ham United FC v SC Heerenveen 28/07/1999 | £7.50 | |
| Charlton Athletic FC v West Ham United FC 30/07/1999 | £6.00 | |
| West Ham United FC v Tottenham Hotspur FC 07/08/1999 | £5.50 | |
| West Ham United FC v Tottenham Hotspur FC 07/08/1999 | £5.00 | |
| West Ham United FC v Metz 10/08/1999 | £8.50 | |
| 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 |