| 2. Round | 06/10/2020 | Chesterfield FC | - | Hartlepool United | 1:2 | ||||
| 3. Round | 10/10/2020 | Chesterfield FC | - | Woking FC | 4:0 | ||||
| 4. Round | 13/10/2020 | Torquay United | - | Chesterfield FC | 2:1 | ||||
| 5. Round | 17/10/2020 | Chesterfield FC | - | Stockport County | 1:2 | ||||
| 1. Round | 20/10/2020 | Wealdstone FC | - | Chesterfield FC | 3:2 | ||||
| 7. Round | 31/10/2020 | Yeovil Town | - | Chesterfield FC | 0:1 | ||||
| 8. Round | 14/11/2020 | Chesterfield FC | - | Maidenhead United | 1:2 |  |
England