| 14. Journée | 08.12.2020 | Sutton United | - | Chesterfield FC | 0:1 |  |
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| 15. Journée | 12.12.2020 | Chesterfield FC | - | Barnet FC | 6:0 | ||||
| 18. Journée | 02.01.2021 | Chesterfield FC | - | Solihull Moors | 1:0 | ||||
| 16. Journée | 05.01.2021 | Solihull Moors | - | Chesterfield FC | 2:1 | |
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| 26. Journée | 20.02.2021 | Notts County | - | Chesterfield FC | 0:1 | ||||
| 27. Journée | 23.02.2021 | Chesterfield FC | - | Altrincham FC | 1:0 | ||||
| 28. Journée | 27.02.2021 | Stockport County | - | Chesterfield FC | 2:0 | ||||
| 29. Journée | 06.03.2021 | Chesterfield FC | - | Yeovil Town | 3:0 | ||||
| 31. Journée | 13.03.2021 | Maidenhead United | - | Chesterfield FC | 2:0 | ||||
| 32. Journée | 16.03.2021 | Chesterfield FC | - | Sutton United | 0:1 | |
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| 23. Journée | 20.04.2021 | Chesterfield FC | - | Halifax Town | 1:2 | ||||
| 40. Journée | 24.04.2021 | Wrexham AFC | - | Chesterfield FC | 0:0 | ||||
| 19. Journée | 27.04.2021 | Bromley FC | - | Chesterfield FC | 1:2 | ||||
| 41. Journée | 01.05.2021 | Hartlepool United | - | Chesterfield FC | 3:1 | ||||
| 45. Journée | 22.05.2021 | Chesterfield FC | - | Dagenham & Redbridge | 2:1 | ||||
| 46. Journée | 29.05.2021 | Halifax Town | - | Chesterfield FC | 1:2 |
Angleterre