| 1. Round | 16/08/2003 | Birmingham City | - | Tottenham Hotspur | 1:0 | ||||
| 2. Round | 23/08/2003 | Tottenham Hotspur | - | Leeds United | 2:1 | ||||
| 3. Round | 27/08/2003 | Liverpool FC | - | Tottenham Hotspur | 0:0 | ||||
| 4. Round | 30/08/2003 | Tottenham Hotspur | - | Fulham FC | 0:3 | ||||
| 5. Round | 13/09/2003 | Chelsea FC | - | Tottenham Hotspur | 4:2 |  |
|||
| 6. Round | 20/09/2003 | Tottenham Hotspur | - | Southampton FC | 1:3 | ||||
| 9. Round | 19/10/2003 | Leicester City | - | Tottenham Hotspur | 1:2 | ||||
| 10. Round | 26/10/2003 | Tottenham Hotspur | - | Middlesbrough FC | 0:0 | ||||
| 11. Round | 01/11/2003 | Tottenham Hotspur | - | Bolton Wanderers | 0:1 | ||||
| 12. Round | 08/11/2003 | Arsenal FC | - | Tottenham Hotspur | 2:1 | ||||
| 13. Round | 23/11/2003 | Tottenham Hotspur | - | Aston Villa | 2:1 | ||||
| 14. Round | 29/11/2003 | Blackburn Rovers | - | Tottenham Hotspur | 1:0 | ||||
| 18. Round | 26/12/2003 | Portsmouth FC | - | Tottenham Hotspur | 2:0 | ||||
| 19. Round | 28/12/2003 | Tottenham Hotspur | - | Charlton Athletic | 0:1 | ||||
| 22. Round | 17/01/2004 | Tottenham Hotspur | - | Liverpool FC | 2:1 | ||||
| 23. Round | 31/01/2004 | Fulham FC | - | Tottenham Hotspur | 2:1 |
England
