| 12. Jornada | 21.09.2019 | Sutton United | - | Chesterfield FC | 4:0 | ||||
| 13. Jornada | 24.09.2019 | Hartlepool United | - | Chesterfield FC | 1:1 | ||||
| 14. Jornada | 28.09.2019 | Chesterfield FC | - | Aldershot Town | 2:1 | ||||
| 15. Jornada | 05.10.2019 | Chesterfield FC | - | Eastleigh FC | 1:2 | ||||
| 17. Jornada | 15.10.2019 | Wrexham AFC | - | Chesterfield FC | 0:1 | ||||
| 18. Jornada | 26.10.2019 | Chesterfield FC | - | Notts County | 1:0 |  |
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| 20. Jornada | 02.11.2019 | Ebbsfleet United | - | Chesterfield FC | 2:2 | ||||
| 22. Jornada | 23.11.2019 | Harrogate Town | - | Chesterfield FC | 3:1 |  |
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| 23. Jornada | 26.11.2019 | Chesterfield FC | - | Hartlepool United | 1:5 | ||||
| 24. Jornada | 30.11.2019 | Aldershot Town | - | Chesterfield FC | 2:2 | ||||
| 25. Jornada | 07.12.2019 | Chesterfield FC | - | Bromley FC | 1:2 | ||||
| 19. Jornada | 10.12.2019 | Chesterfield FC | - | Yeovil Town | 1:2 | ||||
| 26. Jornada | 21.12.2019 | Torquay United | - | Chesterfield FC | 0:3 | ||||
| 27. Jornada | 26.12.2019 | Chesterfield FC | - | Solihull Moors | 2:2 | |
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| 28. Jornada | 28.12.2019 | Halifax Town | - | Chesterfield FC | 1:0 |
Países Bajos