| 7. Round | 13/09/2014 | Chesterfield FC | - | Scunthorpe United | 4:1 | ||||
| 8. Round | 16/09/2014 | Preston North End | - | Chesterfield FC | 3:3 | ||||
| 10. Round | 27/09/2014 | Chesterfield FC | - | Notts County | 1:1 |  |
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| 11. Round | 04/10/2014 | Chesterfield FC | - | Sheffield United | 3:2 |  |
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| 12. Round | 11/10/2014 | Bristol City | - | Chesterfield FC | 3:2 | ||||
| 13. Round | 18/10/2014 | Chesterfield FC | - | Oldham Athletic | 1:1 | ||||
| 14. Round | 21/10/2014 | Colchester United | - | Chesterfield FC | 2:1 | ||||
| 15. Round | 25/10/2014 | Walsall FC | - | Chesterfield FC | 1:0 | ||||
| 6. Round | 28/10/2014 | Chesterfield FC | - | Swindon Town | 0:3 | ||||
| 16. Round | 01/11/2014 | Chesterfield FC | - | Yeovil Town | 0:0 | ||||
| 18. Round | 22/11/2014 | Chesterfield FC | - | Barnsley FC | 2:1 | ||||
| 19. Round | 29/11/2014 | Crawley Town | - | Chesterfield FC | 1:1 | ||||
| 20. Round | 13/12/2014 | Chesterfield FC | - | Bradford City | 0:1 |
Austria