| 26. Jornada | 17.01.2009 | Chester City | - | Chesterfield FC | 1:3 | ||||
| 27. Jornada | 24.01.2009 | Chesterfield FC | - | Morecambe FC | 1:2 | ||||
| 28. Jornada | 28.01.2009 | Chesterfield FC | - | Exeter City | 2:1 | ||||
| 29. Jornada | 31.01.2009 | Notts County | - | Chesterfield FC | 0:1 | ||||
| 32. Jornada | 14.02.2009 | Shrewsbury Town | - | Chesterfield FC | 2:1 | ||||
| 33. Jornada | 20.02.2009 | Chesterfield FC | - | Bournemouth | 1:0 | ||||
| 38. Jornada | 14.03.2009 | Chesterfield FC | - | Dagenham & Redbridge | 1:1 | ||||
| 39. Jornada | 21.03.2009 | Rotherham United | - | Chesterfield FC | 3:0 | ||||
| 25. Jornada | 25.03.2009 | Chesterfield FC | - | Rochdale AFC | 3:0 | ||||
| 40. Jornada | 28.03.2009 | Chesterfield FC | - | Port Vale FC | 2:1 | ||||
| 30. Jornada | 31.03.2009 | Aldershot Town | - | Chesterfield FC | 1:1 | ||||
| 31. Jornada | 07.04.2009 | Chesterfield FC | - | Lincoln City | 1:1 | ||||
| 42. Jornada | 11.04.2009 | Chesterfield FC | - | Darlington FC | 0:0 | ||||
| 43. Jornada | 13.04.2009 | Luton Town | - | Chesterfield FC | 0:0 | ||||
| 44. Jornada | 18.04.2009 | Chesterfield FC | - | Gillingham FC | 0:1 | ||||
| 46. Jornada | 02.05.2009 | Chesterfield FC | - | Bradford City | 0:2 |
Inglaterra