| 33. Round | 16/02/2008 | Hereford United | - | Chesterfield FC | 2:0 | ||||
| 34. Round | 23/02/2008 | Chesterfield FC | - | Brentford FC | 1:0 | ||||
| 35. Round | 01/03/2008 | Rochdale AFC | - | Chesterfield FC | 0:1 | ||||
| 36. Round | 07/03/2008 | Chesterfield FC | - | Lincoln City | 4:1 |  |
|||
| 37. Round | 10/03/2008 | Chesterfield FC | - | Milton Keynes Dons | 1:2 |  |
|||
| 38. Round | 15/03/2008 | Rotherham United | - | Chesterfield FC | 2:1 | |
|||
| 39. Round | 22/03/2008 | Chesterfield FC | - | Accrington Stanley | 4:2 | ||||
| 40. Round | 24/03/2008 | Bradford City | - | Chesterfield FC | 1:0 | ||||
| 41. Round | 29/03/2008 | Dagenham & Redbridge | - | Chesterfield FC | 0:3 | |
|||
| 42. Round | 05/04/2008 | Chesterfield FC | - | Shrewsbury Town | 4:1 | ||||
| 43. Round | 12/04/2008 | Morecambe FC | - | Chesterfield FC | 1:1 | ||||
| 45. Round | 26/04/2008 | Macclesfield Town | - | Chesterfield FC | 1:0 | ||||
| 46. Round | 03/05/2008 | Chesterfield FC | - | Notts County | 1:1 |
England