| 1. Round | 06/08/2022 | Dorking Wanderers | - | Chesterfield FC | 2:2 |  |
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| 5. Round | 26/08/2022 | Chesterfield FC | - | Barnet FC | 3:1 | ||||
| 6. Round | 29/08/2022 | Altrincham FC | - | Chesterfield FC | 1:2 | ||||
| 7. Round | 03/09/2022 | Oldham Athletic | - | Chesterfield FC | 0:2 | ||||
| 9. Round | 13/09/2022 | Chesterfield FC | - | Southend United | 3:2 | ||||
| 10. Round | 17/09/2022 | Yeovil Town | - | Chesterfield FC | 2:2 | ||||
| 11. Round | 24/09/2022 | Maidstone United | - | Chesterfield FC | 1:2 | ||||
| 12. Round | 01/10/2022 | Chesterfield FC | - | Maidenhead United | 1:2 | ||||
| 13. Round | 04/10/2022 | Chesterfield FC | - | Dagenham & Redbridge | 2:3 | ||||
| 29. Round | 24/01/2023 | Chesterfield FC | - | Altrincham FC | 1:0 | ||||
| 30. Round | 28/01/2023 | Barnet FC | - | Chesterfield FC | 3:0 | ||||
| 31. Round | 04/02/2023 | Boreham Wood | - | Chesterfield FC | 1:0 | ||||
| 21. Round | 07/02/2023 | Chesterfield FC | - | Woking FC | 1:3 |
Brazil
Italy 
