| 1. Round | 08/08/2009 | Carlisle United | - | Brentford FC | 1:3 | ||||
| 2. Round | 15/08/2009 | Millwall FC | - | Carlisle United | 0:0 |  |
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| 3. Round | 18/08/2009 | Stockport County | - | Carlisle United | 1:2 | ||||
| 4. Round | 22/08/2009 | Carlisle United | - | Exeter City | 0:1 | |
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| 5. Round | 29/08/2009 | Leyton Orient | - | Carlisle United | 2:2 | ||||
| 6. Round | 05/09/2009 | Carlisle United | - | Tranmere Rovers | 3:0 | ||||
| 7. Round | 12/09/2009 | Carlisle United | - | Brighton & Hove Albion | 0:2 | ||||
| 8. Round | 19/09/2009 | Oldham Athletic | - | Carlisle United | 2:0 | ||||
| 9. Round | 26/09/2009 | Carlisle United | - | Southampton FC | 1:1 | ||||
| 10. Round | 29/09/2009 | Leeds United | - | Carlisle United | 1:1 | ||||
| 11. Round | 03/10/2009 | Walsall FC | - | Carlisle United | 2:2 | ||||
| 12. Round | 10/10/2009 | Carlisle United | - | Norwich City | 0:1 | ||||
| 13. Round | 17/10/2009 | Yeovil Town | - | Carlisle United | 3:1 | ||||
| 14. Round | 24/10/2009 | Carlisle United | - | Southend United | 2:1 | ||||
| 15. Round | 31/10/2009 | Carlisle United | - | Charlton Athletic | 3:1 | ||||
| 16. Round | 14/11/2009 | Bristol Rovers | - | Carlisle United | 3:2 | ||||
| 17. Round | 21/11/2009 | Carlisle United | - | Swindon Town | 0:1 |
England