| 1. Journée | 09.08.2008 | Barnet FC | - | Chesterfield FC | 1:3 | ||||
| 2. Journée | 16.08.2008 | Chesterfield FC | - | Bury FC | 1:3 | ||||
| 3. Journée | 23.08.2008 | Grimsby Town | - | Chesterfield FC | 0:1 |  |
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| 4. Journée | 30.08.2008 | Chesterfield FC | - | Wycombe Wanderers | 0:1 | ||||
| 6. Journée | 13.09.2008 | Dagenham & Redbridge | - | Chesterfield FC | 3:0 | ||||
| 7. Journée | 20.09.2008 | Rochdale AFC | - | Chesterfield FC | 2:1 | ||||
| 8. Journée | 27.09.2008 | Chesterfield FC | - | Brentford FC | 0:1 | ||||
| 9. Journée | 04.10.2008 | Morecambe FC | - | Chesterfield FC | 2:2 | ||||
| 11. Journée | 18.10.2008 | Lincoln City | - | Chesterfield FC | 3:1 | |
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| 13. Journée | 25.10.2008 | Chesterfield FC | - | Notts County | 3:1 |  |
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| 14. Journée | 28.10.2008 | Exeter City | - | Chesterfield FC | 1:6 | ||||
| 15. Journée | 01.11.2008 | AFC Bournemouth | - | Chesterfield FC | 1:1 | ||||
| 17. Journée | 22.11.2008 | Chesterfield FC | - | Accrington Stanley | 1:1 | ||||
| 20. Journée | 12.12.2008 | Chesterfield FC | - | Macclesfield Town | 2:4 | ||||
| 21. Journée | 20.12.2008 | Port Vale FC | - | Chesterfield FC | 0:1 | |
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| 22. Journée | 26.12.2008 | Chesterfield FC | - | Luton Town | 2:2 | ||||
| 27. Journée | 24.01.2009 | Chesterfield FC | - | Morecambe FC | 1:2 |
Angleterre