| 6. Round | 03/09/2016 | AFC Wimbledon | - | Chesterfield FC | 2:1 | ||||
| 7. Round | 10/09/2016 | Oldham Athletic | - | Chesterfield FC | 0:0 |  |
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| 8. Round | 17/09/2016 | Chesterfield FC | - | Northampton Town | 3:1 |  |
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| 9. Round | 24/09/2016 | Bury FC | - | Chesterfield FC | 2:1 | ||||
| 10. Round | 27/09/2016 | Chesterfield FC | - | Gillingham FC | 3:3 | |
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| 11. Round | 01/10/2016 | Chesterfield FC | - | Bradford City | 0:1 | ||||
| 13. Round | 15/10/2016 | Southend United | - | Chesterfield FC | 1:0 | ||||
| 21. Round | 10/12/2016 | Peterborough United | - | Chesterfield FC | 5:2 | ||||
| 23. Round | 26/12/2016 | Rochdale AFC | - | Chesterfield FC | 3:0 | ||||
| 24. Round | 30/12/2016 | Port Vale FC | - | Chesterfield FC | 1:0 | ||||
| 25. Round | 02/01/2017 | Chesterfield FC | - | Milton Keynes Dons | 0:0 | ||||
| 26. Round | 07/01/2017 | Bradford City | - | Chesterfield FC | 2:0 |
England