1. Round | 15/08/1998 | Sheffield Wednesday | - | West Ham United | 0:1 | ||||
2. Round | 22/08/1998 | West Ham United | - | Manchester United | 0:0 | ||||
3. Round | 29/08/1998 | Coventry City | - | West Ham United | 0:0 | ||||
4. Round | 09/09/1998 | West Ham United | - | Wimbledon FC | 3:4 | ||||
5. Round | 12/09/1998 | West Ham United | - | Liverpool FC | 2:1 | ||||
7. Round | 28/09/1998 | West Ham United | - | Southampton FC | 1:0 | ||||
15. Round | 28/11/1998 | West Ham United | - | Tottenham Hotspur | 2:1 | ||||
16. Round | 05/12/1998 | Leeds United | - | West Ham United | 4:0 | ||||
17. Round | 12/12/1998 | Middlesbrough FC | - | West Ham United | 1:0 | ||||
19. Round | 26/12/1998 | Arsenal FC | - | West Ham United | 1:0 | ||||
20. Round | 28/12/1998 | West Ham United | - | Coventry City | 2:0 | ||||
21. Round | 10/01/1999 | Manchester United | - | West Ham United | 4:1 | ||||
25. Round | 13/02/1999 | West Ham United | - | Nottingham Forest | 2:1 | ||||
26. Round | 20/02/1999 | Liverpool FC | - | West Ham United | 2:2 | ||||
35. Round | 24/04/1999 | Tottenham Hotspur | - | West Ham United | 1:2 |