| 2. Journée | 15.08.2009 | Chesterfield FC | - | Northampton Town | 1:0 | ||||
| 3. Journée | 19.08.2009 | Chesterfield FC | - | Notts County | 2:1 | ||||
| 6. Journée | 05.09.2009 | Rotherham United | - | Chesterfield FC | 3:1 |  |
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| 7. Journée | 12.09.2009 | Dagenham & Redbridge | - | Chesterfield FC | 2:1 | ||||
| 8. Journée | 19.09.2009 | Chesterfield FC | - | Macclesfield Town | 4:1 | ||||
| 9. Journée | 26.09.2009 | Bradford City | - | Chesterfield FC | 3:0 | ||||
| 10. Journée | 30.09.2009 | Chesterfield FC | - | Grimsby Town | 3:2 | |
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| 11. Journée | 03.10.2009 | Chesterfield FC | - | Accrington Stanley | 1:0 | ||||
| 14. Journée | 24.10.2009 | Chesterfield FC | - | Burton Albion | 5:2 | |
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| 15. Journée | 31.10.2009 | Chesterfield FC | - | Barnet FC | 1:0 | |
Écosse