| 31. Round | 09/02/2008 | Grimsby Town | - | Chesterfield FC | 4:2 |  |
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| 32. Round | 13/02/2008 | Chesterfield FC | - | Peterborough United | 1:2 | ||||
| 33. Round | 16/02/2008 | Hereford United | - | Chesterfield FC | 2:0 | ||||
| 36. Round | 07/03/2008 | Chesterfield FC | - | Lincoln City | 4:1 | ||||
| 38. Round | 15/03/2008 | Rotherham United | - | Chesterfield FC | 2:1 | ||||
| 42. Round | 05/04/2008 | Chesterfield FC | - | Shrewsbury Town | 4:1 | ||||
| 43. Round | 12/04/2008 | Morecambe FC | - | Chesterfield FC | 1:1 |
England