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