| 1. Ronde | 09.08.2008 | Barnet FC | - | Chesterfield FC | 1:3 |  |
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| 2. Ronde | 16.08.2008 | Chesterfield FC | - | Bury FC | 1:3 | ||||
| 3. Ronde | 23.08.2008 | Grimsby Town | - | Chesterfield FC | 0:1 | ||||
| 5. Ronde | 06.09.2008 | Chesterfield FC | - | Rotherham United | 1:0 | ||||
| 6. Ronde | 13.09.2008 | Dagenham & Redbridge | - | Chesterfield FC | 3:0 |  |
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| 10. Ronde | 11.10.2008 | Chesterfield FC | - | Chester City | 1:1 | ||||
| 11. Ronde | 18.10.2008 | Lincoln City | - | Chesterfield FC | 3:1 | ||||
| 12. Ronde | 22.10.2008 | Chesterfield FC | - | Aldershot Town | 5:1 | |
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| 13. Ronde | 25.10.2008 | Chesterfield FC | - | Notts County | 3:1 | ||||
| 14. Ronde | 28.10.2008 | Exeter City | - | Chesterfield FC | 1:6 | ||||
| 15. Ronde | 01.11.2008 | AFC Bournemouth | - | Chesterfield FC | 1:1 | ||||
| 16. Ronde | 14.11.2008 | Chesterfield FC | - | Shrewsbury Town | 2:2 | ||||
| 17. Ronde | 22.11.2008 | Chesterfield FC | - | Accrington Stanley | 1:1 | ||||
| 18. Ronde | 25.11.2008 | Bradford City | - | Chesterfield FC | 3:2 | |
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| 19. Ronde | 06.12.2008 | Gillingham FC | - | Chesterfield FC | 2:1 | |
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| 20. Ronde | 12.12.2008 | Chesterfield FC | - | Macclesfield Town | 2:4 |
Wales