| 2. Journée | 06.10.2020 | Chesterfield FC | - | Hartlepool United | 1:2 | ||||
| 3. Journée | 10.10.2020 | Chesterfield FC | - | Woking FC | 4:0 | ||||
| 4. Journée | 13.10.2020 | Torquay United | - | Chesterfield FC | 2:1 | ||||
| 5. Journée | 17.10.2020 | Chesterfield FC | - | Stockport County | 1:2 | ||||
| 1. Journée | 20.10.2020 | Wealdstone FC | - | Chesterfield FC | 3:2 | ||||
| 7. Journée | 31.10.2020 | Yeovil Town | - | Chesterfield FC | 0:1 | ||||
| 8. Journée | 14.11.2020 | Chesterfield FC | - | Maidenhead United | 1:2 | ||||
| 11. Journée | 28.11.2020 | Weymouth FC | - | Chesterfield FC | 1:2 |  |
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| 12. Journée | 01.12.2020 | Chesterfield FC | - | Aldershot Town | 0:0 | ||||
| 14. Journée | 08.12.2020 | Sutton United | - | Chesterfield FC | 0:1 | ||||
| 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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