| 6. Ronde | 03.09.2016 | AFC Wimbledon | - | Chesterfield FC | 2:1 | ||||
| 7. Ronde | 10.09.2016 | Oldham Athletic | - | Chesterfield FC | 0:0 |  |
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| 8. Ronde | 17.09.2016 | Chesterfield FC | - | Northampton Town | 3:1 |  |
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| 9. Ronde | 24.09.2016 | Bury FC | - | Chesterfield FC | 2:1 | ||||
| 10. Ronde | 27.09.2016 | Chesterfield FC | - | Gillingham FC | 3:3 | |
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| 11. Ronde | 01.10.2016 | Chesterfield FC | - | Bradford City | 0:1 | ||||
| 13. Ronde | 15.10.2016 | Southend United | - | Chesterfield FC | 1:0 | ||||
| 21. Ronde | 10.12.2016 | Peterborough United | - | Chesterfield FC | 5:2 | ||||
| 23. Ronde | 26.12.2016 | Rochdale AFC | - | Chesterfield FC | 3:0 | ||||
| 24. Ronde | 30.12.2016 | Port Vale FC | - | Chesterfield FC | 1:0 | ||||
| 25. Ronde | 02.01.2017 | Chesterfield FC | - | Milton Keynes Dons | 0:0 | ||||
| 26. Ronde | 07.01.2017 | Bradford City | - | Chesterfield FC | 2:0 |
Engeland