| 1. Round | 09/08/2003 | Carlisle United | - | York City | 1:2 | ||||
| 3. Round | 23/08/2003 | Carlisle United | - | Bristol Rovers | 0:2 | ||||
| 4. Round | 25/08/2003 | Boston United | - | Carlisle United | 1:0 | ||||
| 5. Round | 30/08/2003 | Carlisle United | - | Cambridge United | 0:0 | ||||
| 6. Round | 06/09/2003 | Darlington FC | - | Carlisle United | 2:0 |  |
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| 8. Round | 16/09/2003 | Northampton Town | - | Carlisle United | 2:0 | ||||
| 9. Round | 20/09/2003 | Southend United | - | Carlisle United | 2:2 | ||||
| 10. Round | 27/09/2003 | Carlisle United | - | Swansea City | 1:2 | ||||
| 11. Round | 30/09/2003 | Carlisle United | - | Leyton Orient | 0:1 | ||||
| 12. Round | 04/10/2003 | Kidderminster Harriers | - | Carlisle United | 2:1 | ||||
| 14. Round | 18/10/2003 | Carlisle United | - | Macclesfield Town | 0:1 | ||||
| 15. Round | 21/10/2003 | Carlisle United | - | Scunthorpe United | 1:4 | ||||
| 16. Round | 25/10/2003 | Huddersfield Town | - | Carlisle United | 2:1 | ||||
| 17. Round | 01/11/2003 | Lincoln City | - | Carlisle United | 2:0 | |
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| 18. Round | 15/11/2003 | Carlisle United | - | Mansfield Town | 0:2 |
Scotland