| 26. Round | 11/01/2014 | Chesterfield FC | - | Bury FC | 4:0 |  |
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| 27. Round | 18/01/2014 | Southend United | - | Chesterfield FC | 3:0 | ||||
| 24. Round | 25/01/2014 | Northampton Town | - | Chesterfield FC | 1:3 | |
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| 29. Round | 28/01/2014 | York City | - | Chesterfield FC | 0:2 | ||||
| 30. Round | 01/02/2014 | Chesterfield FC | - | Bristol Rovers | 3:1 | ||||
| 31. Round | 08/02/2014 | Scunthorpe United | - | Chesterfield FC | 1:1 | ||||
| 32. Round | 15/02/2014 | Chesterfield FC | - | Torquay United | 3:1 | ||||
| 33. Round | 22/02/2014 | Wycombe Wanderers | - | Chesterfield FC | 1:0 | ||||
| 25. Round | 25/02/2014 | Cheltenham Town | - | Chesterfield FC | 1:4 | |
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| 34. Round | 03/03/2014 | Chesterfield FC | - | Portsmouth FC | 0:0 | ||||
| 35. Round | 08/03/2014 | Accrington Stanley | - | Chesterfield FC | 3:1 | ||||
| 42. Round | 12/04/2014 | Hartlepool United | - | Chesterfield FC | 1:2 | ||||
| 43. Round | 18/04/2014 | Chesterfield FC | - | Exeter City | 1:1 | ||||
| 44. Round | 21/04/2014 | Dagenham & Redbridge | - | Chesterfield FC | 0:1 | ||||
| 45. Round | 27/04/2014 | Burton Albion | - | Chesterfield FC | 0:2 | ||||
| 46. Round | 03/05/2014 | Chesterfield FC | - | Fleetwood Town | 2:1 |
England