| 1. Round | 08/08/2009 | Aldershot Town | - | Darlington FC | 3:1 |  |
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| 2. Round | 15/08/2009 | Darlington FC | - | Bury FC | 0:1 | ||||
| 3. Round | 18/08/2009 | Darlington FC | - | Crewe Alexandra | 0:1 | ||||
| 4. Round | 22/08/2009 | Port Vale FC | - | Darlington FC | 1:0 | |
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| 5. Round | 29/08/2009 | Darlington FC | - | Cheltenham Town | 1:1 | ||||
| 6. Round | 05/09/2009 | Lincoln City | - | Darlington FC | 3:0 | ||||
| 7. Round | 11/09/2009 | Accrington Stanley | - | Darlington FC | 2:1 | ||||
| 8. Round | 19/09/2009 | Darlington FC | - | AFC Bournemouth | 0:2 | ||||
| 9. Round | 26/09/2009 | Grimsby Town | - | Darlington FC | 1:1 |  |
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| 12. Round | 10/10/2009 | Dagenham & Redbridge | - | Darlington FC | 2:0 | ||||
| 13. Round | 17/10/2009 | Darlington FC | - | Shrewsbury Town | 2:1 | |
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| 14. Round | 24/10/2009 | Barnet FC | - | Darlington FC | 3:0 | ||||
| 15. Round | 31/10/2009 | Hereford United | - | Darlington FC | 2:1 | ||||
| 16. Round | 14/11/2009 | Darlington FC | - | Burton Albion | 1:0 | |
England