6. Round | 28/08/1999 | Tottenham Hotspur | - | Leeds United | 1:2 | ||||
7. Round | 12/09/1999 | Bradford City | - | Tottenham Hotspur | 1:1 | ||||
8. Round | 19/09/1999 | Tottenham Hotspur | - | Coventry City | 3:2 | ||||
9. Round | 26/09/1999 | Wimbledon FC | - | Tottenham Hotspur | 1:1 | ||||
10. Round | 03/10/1999 | Tottenham Hotspur | - | Leicester City | 2:3 | ||||
11. Round | 16/10/1999 | Derby County | - | Tottenham Hotspur | 0:1 | ||||
17. Round | 06/12/1999 | Tottenham Hotspur | - | West Ham United | 0:0 | ||||
18. Round | 18/12/1999 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
19. Round | 26/12/1999 | Tottenham Hotspur | - | Watford FC | 4:0 | ||||
20. Round | 29/12/1999 | Aston Villa | - | Tottenham Hotspur | 1:1 | ||||
22. Round | 15/01/2000 | Everton FC | - | Tottenham Hotspur | 2:2 | ||||
23. Round | 22/01/2000 | Tottenham Hotspur | - | Sheffield Wednesday | 0:1 | ||||
24. Round | 05/02/2000 | Tottenham Hotspur | - | Chelsea FC | 0:1 | ||||
25. Round | 12/02/2000 | Leeds United | - | Tottenham Hotspur | 1:0 |