| 1. Round | 06/08/2022 | Dorking Wanderers | - | Chesterfield FC | 2:2 |  |
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| 3. Round | 16/08/2022 | Chesterfield FC | - | Wrexham AFC | 2:0 | ||||
| 4. Round | 20/08/2022 | Notts County | - | Chesterfield FC | 2:2 | |
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| 5. Round | 26/08/2022 | Chesterfield FC | - | Barnet FC | 3:1 | |
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| 6. Round | 29/08/2022 | Altrincham FC | - | Chesterfield FC | 1:2 | ||||
| 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 | ||||
| 14. Round | 08/10/2022 | Eastleigh FC | - | Chesterfield FC | 2:1 | ||||
| 16. Round | 25/10/2022 | York City | - | Chesterfield FC | 1:1 | ||||
| 23. Round | 10/12/2022 | Chesterfield FC | - | Dorking Wanderers | 3:1 | ||||
| 26. Round | 01/01/2023 | Chesterfield FC | - | Scunthorpe United | 4:1 | |
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| 29. Round | 24/01/2023 | Chesterfield FC | - | Altrincham FC | 1:0 | ||||
| 30. Round | 28/01/2023 | Barnet FC | - | Chesterfield FC | 3:0 | ||||
| 42. Round | 07/04/2023 | Chesterfield FC | - | York City | 1:3 | ||||
| 43. Round | 10/04/2023 | Dagenham & Redbridge | - | Chesterfield FC | 0:1 |
Netherlands
Ghana