| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £2.00 | |
| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £4.50 | |
| 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 | |
| Aston Villa FC v West Ham United FC 16/08/1999 | £3.50 | |
| Liverpool FC v West Ham United FC 27/10/1999 | £4.00 | |
| Chelsea FC v West Ham United FC 07/11/1999 | £3.50 | |
| Chelsea FC v West Ham United FC 07/11/1999 | £3.00 | |
| Tottenham Hotspur FC v West Ham United FC 06/12/1999 | £4.50 | |
| West Ham United FC v Derby County FC 28/12/1999 | £4.50 | |
| Southampton FC v West Ham United FC 05/02/2000 | £4.50 | |
| Southampton FC v West Ham United FC 05/02/2000 | £2.00 |