| Liverpool FC v West Ham United FC 27/10/1999 | £4.00 | |
| West Ham United FC v Steaua Bucharest 04/11/1999 | £5.00 | |
| Chelsea FC v West Ham United FC 07/11/1999 | £3.50 | |
| Chelsea FC v West Ham United FC 07/11/1999 | £3.00 | |
| Chelsea FC v West Ham United FC 07/11/1999 | £5.00 | |
| West Ham United FC v Sheffield Wednesday FC 21/11/1999 | £5.00 | |
| West Ham United FC v Liverpool FC 27/11/1999 | £5.00 | |
| Birmingham City FC v West Ham United FC 30/11/1999 | £5.00 | |
| Tottenham Hotspur FC v West Ham United FC 06/12/1999 | £4.50 | |
| Tottenham Hotspur FC v West Ham United FC 06/12/1999 | £3.50 | |
| Tranmere Rovers FC v West Ham United FC 11/12/1999 | £7.50 | |
| Wimbledon v West Ham United FC 26/12/1999 | £6.50 |