| 12. Round | 10/10/2009 | AFC Bournemouth | - | Chesterfield FC | 1:2 | ||||
| 13. Round | 17/10/2009 | Hereford United | - | Chesterfield FC | 1:0 | ||||
| 14. Round | 24/10/2009 | Chesterfield FC | - | Burton Albion | 5:2 | ||||
| 15. Round | 31/10/2009 | Chesterfield FC | - | Barnet FC | 1:0 | ||||
| 16. Round | 14/11/2009 | Rochdale AFC | - | Chesterfield FC | 2:3 | ||||
| 17. Round | 21/11/2009 | Chesterfield FC | - | Darlington FC | 5:2 |  |
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| 18. Round | 24/11/2009 | Bury FC | - | Chesterfield FC | 2:1 | ||||
| 19. Round | 02/12/2009 | Chesterfield FC | - | Crewe Alexandra | 2:3 | ||||
| 20. Round | 05/12/2009 | Aldershot Town | - | Chesterfield FC | 1:0 | ||||
| 21. Round | 12/12/2009 | Chesterfield FC | - | Cheltenham Town | 1:0 | ||||
| 23. Round | 26/12/2009 | Lincoln City | - | Chesterfield FC | 2:1 | ||||
| 25. Round | 02/01/2010 | Chesterfield FC | - | Shrewsbury Town | 0:1 |
England
Jamaica 