| 11. Round | 17/10/1999 | Middlesbrough FC | - | West Ham United | 2:0 | ||||
| 14. Round | 07/11/1999 | Chelsea FC | - | West Ham United | 0:0 | ||||
| 23. Round | 22/01/2000 | Leicester City | - | West Ham United | 1:3 | ||||
| 24. Round | 05/02/2000 | Southampton FC | - | West Ham United | 2:1 | ||||
| 27. Round | 04/03/2000 | Watford FC | - | West Ham United | 1:2 | ||||
| 5. Round | 08/03/2000 | West Ham United | - | Southampton FC | 2:0 | ||||
| 28. Round | 11/03/2000 | Sheffield Wednesday | - | West Ham United | 3:1 | ||||
| 29. Round | 18/03/2000 | West Ham United | - | Chelsea FC | 0:0 | ||||
| 30. Round | 26/03/2000 | West Ham United | - | Wimbledon FC | 2:1 | ||||
| 31. Round | 01/04/2000 | Manchester United | - | West Ham United | 7:1 | ||||
| 32. Round | 12/04/2000 | West Ham United | - | Newcastle United | 2:1 |
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