| 1. Round | 09/08/2008 | Barnet FC | - | Chesterfield FC | 1:3 | ||||
| 2. Round | 16/08/2008 | Chesterfield FC | - | Bury FC | 1:3 | ||||
| 3. Round | 23/08/2008 | Grimsby Town | - | Chesterfield FC | 0:1 |  |
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| 4. Round | 30/08/2008 | Chesterfield FC | - | Wycombe Wanderers | 0:1 | ||||
| 6. Round | 13/09/2008 | Dagenham & Redbridge | - | Chesterfield FC | 3:0 | ||||
| 7. Round | 20/09/2008 | Rochdale AFC | - | Chesterfield FC | 2:1 | ||||
| 8. Round | 27/09/2008 | Chesterfield FC | - | Brentford FC | 0:1 | ||||
| 9. Round | 04/10/2008 | Morecambe FC | - | Chesterfield FC | 2:2 | ||||
| 11. Round | 18/10/2008 | Lincoln City | - | Chesterfield FC | 3:1 | |
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| 13. Round | 25/10/2008 | Chesterfield FC | - | Notts County | 3:1 |  |
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| 14. Round | 28/10/2008 | Exeter City | - | Chesterfield FC | 1:6 | ||||
| 15. Round | 01/11/2008 | AFC Bournemouth | - | Chesterfield FC | 1:1 | ||||
| 17. Round | 22/11/2008 | Chesterfield FC | - | Accrington Stanley | 1:1 | ||||
| 20. Round | 12/12/2008 | Chesterfield FC | - | Macclesfield Town | 2:4 | ||||
| 21. Round | 20/12/2008 | Port Vale FC | - | Chesterfield FC | 0:1 | |
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| 22. Round | 26/12/2008 | Chesterfield FC | - | Luton Town | 2:2 | ||||
| 27. Round | 24/01/2009 | Chesterfield FC | - | Morecambe FC | 1:2 |
England