| 2. Round | 24/08/2003 | Middlesbrough FC | - | Arsenal FC | 0:4 | ||||
| 3. Round | 26/08/2003 | Leicester City | - | Middlesbrough FC | 0:0 | ||||
| 4. Round | 30/08/2003 | Middlesbrough FC | - | Leeds United | 2:3 | ||||
| 5. Round | 13/09/2003 | Bolton Wanderers | - | Middlesbrough FC | 2:0 | ||||
| 10. Round | 26/10/2003 | Tottenham Hotspur | - | Middlesbrough FC | 0:0 | ||||
| 13. Round | 22/11/2003 | Middlesbrough FC | - | Liverpool FC | 0:0 | ||||
| 18. Round | 26/12/2003 | Blackburn Rovers | - | Middlesbrough FC | 2:2 | ||||
| 22. Round | 17/01/2004 | Middlesbrough FC | - | Leicester City | 3:3 | ||||
| 23. Round | 31/01/2004 | Leeds United | - | Middlesbrough FC | 0:3 | ||||
| 27. Round | 09/03/2004 | Middlesbrough FC | - | Tottenham Hotspur | 1:0 |
England