| 2. Round | 15/08/2009 | Chesterfield FC | - | Northampton Town | 1:0 | ||||
| 3. Round | 19/08/2009 | Chesterfield FC | - | Notts County | 2:1 | ||||
| 6. Round | 05/09/2009 | Rotherham United | - | Chesterfield FC | 3:1 |  |
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| 7. Round | 12/09/2009 | Dagenham & Redbridge | - | Chesterfield FC | 2:1 | ||||
| 8. Round | 19/09/2009 | Chesterfield FC | - | Macclesfield Town | 4:1 | ||||
| 9. Round | 26/09/2009 | Bradford City | - | Chesterfield FC | 3:0 | ||||
| 10. Round | 30/09/2009 | Chesterfield FC | - | Grimsby Town | 3:2 | |
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| 11. Round | 03/10/2009 | Chesterfield FC | - | Accrington Stanley | 1:0 | ||||
| 14. Round | 24/10/2009 | Chesterfield FC | - | Burton Albion | 5:2 | |
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| 15. Round | 31/10/2009 | Chesterfield FC | - | Barnet FC | 1:0 | |
Scotland