1. Round | 07/08/1999 | West Ham United | - | Tottenham Hotspur | 1:0 | ||||
2. Round | 09/08/1999 | Tottenham Hotspur | - | Newcastle United | 3:1 | ||||
6. Round | 28/08/1999 | Tottenham Hotspur | - | Leeds United | 1:2 | ||||
8. Round | 19/09/1999 | Tottenham Hotspur | - | Coventry City | 3:2 | ||||
9. Round | 26/09/1999 | Wimbledon FC | - | Tottenham Hotspur | 1:1 | ||||
13. Round | 31/10/1999 | Sunderland AFC | - | Tottenham Hotspur | 2:1 | ||||
14. Round | 07/11/1999 | Tottenham Hotspur | - | Arsenal FC | 2:1 | ||||
15. Round | 20/11/1999 | Southampton FC | - | Tottenham Hotspur | 0:1 | ||||
16. Round | 28/11/1999 | Newcastle United | - | Tottenham Hotspur | 2:1 | ||||
17. Round | 06/12/1999 | Tottenham Hotspur | - | West Ham United | 0:0 | ||||
19. Round | 26/12/1999 | Tottenham Hotspur | - | Watford FC | 4:0 | ||||
25. Round | 12/02/2000 | Leeds United | - | Tottenham Hotspur | 1:0 |