| 12. Ronde | 10.10.2009 | AFC Bournemouth | - | Chesterfield FC | 1:2 | ||||
| 13. Ronde | 17.10.2009 | Hereford United | - | Chesterfield FC | 1:0 | ||||
| 14. Ronde | 24.10.2009 | Chesterfield FC | - | Burton Albion | 5:2 | ||||
| 15. Ronde | 31.10.2009 | Chesterfield FC | - | Barnet FC | 1:0 | ||||
| 16. Ronde | 14.11.2009 | Rochdale AFC | - | Chesterfield FC | 2:3 | ||||
| 17. Ronde | 21.11.2009 | Chesterfield FC | - | Darlington FC | 5:2 |  |
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| 18. Ronde | 24.11.2009 | Bury FC | - | Chesterfield FC | 2:1 | ||||
| 19. Ronde | 02.12.2009 | Chesterfield FC | - | Crewe Alexandra | 2:3 | ||||
| 20. Ronde | 05.12.2009 | Aldershot Town | - | Chesterfield FC | 1:0 | ||||
| 21. Ronde | 12.12.2009 | Chesterfield FC | - | Cheltenham Town | 1:0 | ||||
| 23. Ronde | 26.12.2009 | Lincoln City | - | Chesterfield FC | 2:1 | ||||
| 25. Ronde | 02.01.2010 | Chesterfield FC | - | Shrewsbury Town | 0:1 |
Engeland
Jamaica