| 1. Round | 06/08/2022 | Dorking Wanderers | - | Chesterfield FC | 2:2 | ||||
| 15. Round | 22/10/2022 | Chesterfield FC | - | Bromley FC | 3:2 | ||||
| 16. Round | 25/10/2022 | York City | - | Chesterfield FC | 1:1 | ||||
| 17. Round | 29/10/2022 | Chesterfield FC | - | Boreham Wood | 2:0 | ||||
| 8. Round | 01/11/2022 | Chesterfield FC | - | Gateshead FC | 2:1 | ||||
| 19. Round | 12/11/2022 | Torquay United | - | Chesterfield FC | 1:5 | ||||
| 20. Round | 19/11/2022 | Chesterfield FC | - | Solihull Moors | 2:0 | ||||
| 22. Round | 03/12/2022 | Halifax Town | - | Chesterfield FC | 1:0 |
England