10. Round | 03/10/1999 | West Ham United | - | Arsenal FC | 2:1 | ||||
11. Round | 17/10/1999 | Middlesbrough FC | - | West Ham United | 2:0 | ||||
12. Round | 24/10/1999 | West Ham United | - | Sunderland AFC | 1:1 | ||||
2. Round | 27/10/1999 | Liverpool FC | - | West Ham United | 1:0 | ||||
13. Round | 30/10/1999 | Leeds United | - | West Ham United | 1:0 | ||||
14. Round | 07/11/1999 | Chelsea FC | - | West Ham United | 0:0 | ||||
15. Round | 21/11/1999 | West Ham United | - | Sheffield Wednesday | 4:3 | ||||
16. Round | 27/11/1999 | West Ham United | - | Liverpool FC | 1:0 | ||||
17. Round | 06/12/1999 | Tottenham Hotspur | - | West Ham United | 0:0 | ||||
18. Round | 18/12/1999 | West Ham United | - | Manchester United | 2:4 | ||||
19. Round | 26/12/1999 | Wimbledon FC | - | West Ham United | 2:2 | ||||
23. Round | 22/01/2000 | Leicester City | - | West Ham United | 1:3 | ||||
28. Round | 11/03/2000 | Sheffield Wednesday | - | West Ham United | 3:1 | ||||
29. Round | 18/03/2000 | West Ham United | - | Chelsea FC | 0:0 | ||||
32. Round | 12/04/2000 | West Ham United | - | Newcastle United | 2:1 |