| 3. Round | 19/08/2014 | Chesterfield FC | - | Milton Keynes Dons | 0:1 | ||||
| 10. Round | 27/09/2014 | Chesterfield FC | - | Notts County | 1:1 | ||||
| 13. Round | 18/10/2014 | Chesterfield FC | - | Oldham Athletic | 1:1 |  |
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| 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 | ||||
| 20. Round | 13/12/2014 | Chesterfield FC | - | Bradford City | 0:1 | ||||
| 25. Round | 10/01/2015 | Chesterfield FC | - | Port Vale FC | 3:0 | ||||
| 26. Round | 17/01/2015 | Swindon Town | - | Chesterfield FC | 3:1 | ||||
| 24. Round | 27/01/2015 | Chesterfield FC | - | Crawley Town | 3:0 | ||||
| 28. Round | 31/01/2015 | Chesterfield FC | - | Doncaster Rovers | 2:2 | ||||
| 41. Round | 06/04/2015 | Chesterfield FC | - | Crewe Alexandra | 1:0 | ||||
| 43. Round | 14/04/2015 | Chesterfield FC | - | Colchester United | 6:0 |  |
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| 44. Round | 18/04/2015 | Oldham Athletic | - | Chesterfield FC | 0:0 | ||||
| 45. Round | 25/04/2015 | Chesterfield FC | - | Bristol City | 0:2 | ||||
| 46. Round | 03/05/2015 | Sheffield United | - | Chesterfield FC | 1:1 |
England