| 26. Round | 17/01/2009 | Rotherham United | - | AFC Bournemouth | 1:0 | ||||
| 27. Round | 24/01/2009 | Grimsby Town | - | Rotherham United | 3:0 | ||||
| 28. Round | 27/01/2009 | Darlington FC | - | Rotherham United | 1:0 |  |
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| 29. Round | 31/01/2009 | Rotherham United | - | Macclesfield Town | 2:0 | ||||
| 32. Round | 14/02/2009 | Rotherham United | - | Gillingham FC | 2:0 | ||||
| 39. Round | 21/03/2009 | Rotherham United | - | Chesterfield FC | 3:0 | ||||
| 30. Round | 24/03/2009 | Rotherham United | - | Bury FC | 1:1 | ||||
| 40. Round | 28/03/2009 | Rotherham United | - | Accrington Stanley | 0:0 | ||||
| 25. Round | 31/03/2009 | Luton Town | - | Rotherham United | 2:4 | ||||
| 41. Round | 04/04/2009 | Aldershot Town | - | Rotherham United | 0:1 | ||||
| 31. Round | 07/04/2009 | Barnet FC | - | Rotherham United | 2:0 | ||||
| 44. Round | 18/04/2009 | Rotherham United | - | Shrewsbury Town | 1:2 | ||||
| 35. Round | 21/04/2009 | Rotherham United | - | Morecambe FC | 3:2 |  |
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| 45. Round | 25/04/2009 | Bradford City | - | Rotherham United | 3:0 | ||||
| 46. Round | 02/05/2009 | Rotherham United | - | Exeter City | 0:1 |
England