| 1. Jornada | 08.08.2009 | Torquay United | - | Chesterfield FC | 2:0 | ||||
| 2. Jornada | 15.08.2009 | Chesterfield FC | - | Northampton Town | 1:0 | ||||
| 3. Jornada | 19.08.2009 | Chesterfield FC | - | Notts County | 2:1 |  |
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| 4. Jornada | 22.08.2009 | Shrewsbury Town | - | Chesterfield FC | 1:1 | |
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| 5. Jornada | 29.08.2009 | Chesterfield FC | - | Morecambe FC | 1:1 | ||||
| 6. Jornada | 05.09.2009 | Rotherham United | - | Chesterfield FC | 3:1 | |
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| 7. Jornada | 12.09.2009 | Dagenham & Redbridge | - | Chesterfield FC | 2:1 | ||||
| 8. Jornada | 19.09.2009 | Chesterfield FC | - | Macclesfield Town | 4:1 | |
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| 9. Jornada | 26.09.2009 | Bradford City | - | Chesterfield FC | 3:0 | ||||
| 10. Jornada | 30.09.2009 | Chesterfield FC | - | Grimsby Town | 3:2 | ||||
| 11. Jornada | 03.10.2009 | Chesterfield FC | - | Accrington Stanley | 1:0 | ||||
| 12. Jornada | 10.10.2009 | Bournemouth | - | Chesterfield FC | 1:2 | ||||
| 13. Jornada | 17.10.2009 | Hereford United | - | Chesterfield FC | 1:0 |
Inglaterra