| 5. Jornada | 17.08.2019 | Barnet FC | - | Chesterfield FC | 2:2 | ||||
| 6. Jornada | 24.08.2019 | Chesterfield FC | - | Barrow AFC | 2:2 | ||||
| 7. Jornada | 26.08.2019 | Stockport County | - | Chesterfield FC | 2:0 | ||||
| 8. Jornada | 31.08.2019 | Chesterfield FC | - | Dagenham & Redbridge | 1:1 | ||||
| 9. Jornada | 03.09.2019 | Chesterfield FC | - | Halifax Town | 2:3 | ||||
| 10. Jornada | 07.09.2019 | Bromley FC | - | Chesterfield FC | 2:1 | ||||
| 24. Jornada | 30.11.2019 | Aldershot Town | - | Chesterfield FC | 2:2 |  |
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| 25. Jornada | 07.12.2019 | Chesterfield FC | - | Bromley FC | 1:2 | |
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| 19. Jornada | 10.12.2019 | Chesterfield FC | - | Yeovil Town | 1:2 | ||||
| 26. Jornada | 21.12.2019 | Torquay United | - | Chesterfield FC | 0:3 | |
Inglaterra