| 8. Round | 17/09/2016 | Chesterfield FC | - | Northampton Town | 3:1 | ||||
| 11. Round | 01/10/2016 | Chesterfield FC | - | Bradford City | 0:1 | ||||
| 13. Round | 15/10/2016 | Southend United | - | Chesterfield FC | 1:0 | ||||
| 14. Round | 18/10/2016 | Chesterfield FC | - | Fleetwood Town | 0:1 | ||||
| 15. Round | 22/10/2016 | Chesterfield FC | - | Scunthorpe United | 0:3 | ||||
| 16. Round | 29/10/2016 | Charlton Athletic | - | Chesterfield FC | 1:0 | ||||
| 12. Round | 01/11/2016 | Coventry City | - | Chesterfield FC | 2:0 |
England