| 27. Round | 24/01/2009 | Shrewsbury Town | - | Darlington FC | 1:0 | ||||
| 28. Round | 27/01/2009 | Darlington FC | - | Rotherham United | 1:0 |  |
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| 29. Round | 31/01/2009 | Dagenham & Redbridge | - | Darlington FC | 0:1 |  |
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| 30. Round | 17/02/2009 | Bradford City | - | Darlington FC | 0:0 | |
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| 33. Round | 21/02/2009 | Darlington FC | - | Grimsby Town | 1:0 | ||||
| 19. Round | 24/02/2009 | Darlington FC | - | Rochdale AFC | 1:2 | |
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| 34. Round | 28/02/2009 | Exeter City | - | Darlington FC | 2:0 | ||||
| 35. Round | 03/03/2009 | Darlington FC | - | Notts County | 1:0 | ||||
| 36. Round | 07/03/2009 | Darlington FC | - | Macclesfield Town | 1:2 | ||||
| 37. Round | 10/03/2009 | Gillingham FC | - | Darlington FC | 1:0 | ||||
| 38. Round | 14/03/2009 | Port Vale FC | - | Darlington FC | 3:1 | |
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| 32. Round | 17/03/2009 | Lincoln City | - | Darlington FC | 0:1 | |
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| 39. Round | 21/03/2009 | Darlington FC | - | Aldershot Town | 2:0 | |
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| 25. Round | 24/03/2009 | Accrington Stanley | - | Darlington FC | 1:0 | ||||
| 40. Round | 28/03/2009 | Barnet FC | - | Darlington FC | 0:1 | ||||
| 41. Round | 04/04/2009 | Darlington FC | - | Morecambe FC | 0:0 | ||||
| 31. Round | 07/04/2009 | Darlington FC | - | Wycombe Wanderers | 1:2 |
England