| 3. Round | 10/10/2020 | Chesterfield FC | - | Woking FC | 4:0 | ||||
| 1. Round | 20/10/2020 | Wealdstone FC | - | Chesterfield FC | 3:2 | ||||
| 7. Round | 31/10/2020 | Yeovil Town | - | Chesterfield FC | 0:1 | ||||
| 9. Round | 17/11/2020 | Altrincham FC | - | Chesterfield FC | 3:2 | ||||
| 10. Round | 21/11/2020 | Chesterfield FC | - | Notts County | 2:3 | ||||
| 12. Round | 01/12/2020 | Chesterfield FC | - | Aldershot Town | 0:0 |
England