| 23. Round | 28/12/2008 | Darlington FC | - | Chesterfield FC | 0:0 | ||||
| 24. Round | 03/01/2009 | Darlington FC | - | AFC Bournemouth | 2:1 |  |
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| 26. Round | 17/01/2009 | Darlington FC | - | Luton Town | 5:1 | ||||
| 27. Round | 24/01/2009 | Shrewsbury Town | - | Darlington FC | 1:0 | ||||
| 28. Round | 27/01/2009 | Darlington FC | - | Rotherham United | 1:0 | ||||
| 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 | ||||
| 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 | ||||
| 25. Round | 24/03/2009 | Accrington Stanley | - | Darlington FC | 1:0 | ||||
| 40. Round | 28/03/2009 | Barnet FC | - | Darlington FC | 0:1 | |
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| 41. Round | 04/04/2009 | Darlington FC | - | Morecambe FC | 0:0 | ||||
| 31. Round | 07/04/2009 | Darlington FC | - | Wycombe Wanderers | 1:2 | ||||
| 42. Round | 11/04/2009 | Chesterfield FC | - | Darlington FC | 0:0 | ||||
| 43. Round | 13/04/2009 | Darlington FC | - | Bury FC | 2:2 | |
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| 44. Round | 18/04/2009 | Rochdale AFC | - | Darlington FC | 0:2 | ||||
| 45. Round | 25/04/2009 | Darlington FC | - | Brentford FC | 1:3 | |
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| 46. Round | 02/05/2009 | Chester City | - | Darlington FC | 1:2 | |
England