1. Round | 07/08/1999 | West Ham United | - | Tottenham Hotspur | 1:0 | ||||
3. Round | 16/08/1999 | Aston Villa | - | West Ham United | 2:2 | ||||
4. Round | 21/08/1999 | West Ham United | - | Leicester City | 2:1 | ||||
6. Round | 28/08/1999 | Bradford City | - | West Ham United | 0:3 | ||||
7. Round | 11/09/1999 | West Ham United | - | Watford FC | 1:0 | ||||
26. Round | 26/02/2000 | West Ham United | - | Everton FC | 0:4 | ||||
27. Round | 04/03/2000 | Watford FC | - | West Ham United | 1:2 | ||||
5. Round | 08/03/2000 | West Ham United | - | Southampton FC | 2:0 |