| 28. Ronde | 28.01.2009 | Chesterfield FC | - | Exeter City | 2:1 | ||||
| 29. Ronde | 31.01.2009 | Notts County | - | Chesterfield FC | 0:1 |  |
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| 33. Ronde | 20.02.2009 | Chesterfield FC | - | AFC Bournemouth | 1:0 | ||||
| 34. Ronde | 28.02.2009 | Chesterfield FC | - | Barnet FC | 1:1 | ||||
| 35. Ronde | 03.03.2009 | Bury FC | - | Chesterfield FC | 1:2 |  |
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| 36. Ronde | 07.03.2009 | Wycombe Wanderers | - | Chesterfield FC | 1:1 | ||||
| 37. Ronde | 11.03.2009 | Chesterfield FC | - | Grimsby Town | 2:1 | |
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| 38. Ronde | 14.03.2009 | Chesterfield FC | - | Dagenham & Redbridge | 1:1 | ||||
| 24. Ronde | 17.03.2009 | Brentford FC | - | Chesterfield FC | 0:1 | ||||
| 39. Ronde | 21.03.2009 | Rotherham United | - | Chesterfield FC | 3:0 |  |
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| 40. Ronde | 28.03.2009 | Chesterfield FC | - | Port Vale FC | 2:1 | ||||
| 30. Ronde | 31.03.2009 | Aldershot Town | - | Chesterfield FC | 1:1 | |
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| 41. Ronde | 04.04.2009 | Macclesfield Town | - | Chesterfield FC | 1:1 | ||||
| 31. Ronde | 07.04.2009 | Chesterfield FC | - | Lincoln City | 1:1 | ||||
| 44. Ronde | 18.04.2009 | Chesterfield FC | - | Gillingham FC | 0:1 | ||||
| 45. Ronde | 25.04.2009 | Accrington Stanley | - | Chesterfield FC | 1:0 | ||||
| 46. Ronde | 02.05.2009 | Chesterfield FC | - | Bradford City | 0:2 |
Engeland