| 2. Round | 16/08/2003 | Hartlepool United | - | Tranmere Rovers | 0:0 |  |
|||
| 3. Round | 23/08/2003 | Bristol City | - | Hartlepool United | 1:1 |  |
|||
| 4. Round | 25/08/2003 | Hartlepool United | - | Port Vale FC | 2:0 | |
|||
| 5. Round | 30/08/2003 | Luton Town | - | Hartlepool United | 3:2 | ||||
| 6. Round | 06/09/2003 | Hartlepool United | - | Oldham Athletic | 0:0 | ||||
| 7. Round | 12/09/2003 | Hartlepool United | - | Grimsby Town | 8:1 | |
|
||
| 8. Round | 16/09/2003 | Stockport County | - | Hartlepool United | 1:2 | |
|||
| 9. Round | 20/09/2003 | Brentford FC | - | Hartlepool United | 2:1 | ||||
| 10. Round | 27/09/2003 | Hartlepool United | - | Brighton & Hove Albion | 0:0 | ||||
| 12. Round | 04/10/2003 | AFC Bournemouth | - | Hartlepool United | 2:2 | |
|||
| 13. Round | 10/10/2003 | Hartlepool United | - | Sheffield Wednesday | 1:1 | |
|||
| 14. Round | 18/10/2003 | Blackpool FC | - | Hartlepool United | 4:0 | ||||
| 16. Round | 25/10/2003 | Hartlepool United | - | Wycombe Wanderers | 1:1 | ||||
| 17. Round | 01/11/2003 | Notts County | - | Hartlepool United | 1:0 | |
|||
| 19. Round | 22/11/2003 | Plymouth Argyle | - | Hartlepool United | 2:0 |
England