| 2. Round | 28/08/2021 | Chesterfield FC | - | Wealdstone FC | 2:0 | ||||
| 3. Round | 30/08/2021 | King's Lynn | - | Chesterfield FC | 0:2 |  |
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| 4. Round | 04/09/2021 | Chesterfield FC | - | Bromley FC | 2:2 | ||||
| 6. Round | 14/09/2021 | Chesterfield FC | - | Barnet FC | 4:2 | |
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| 9. Round | 18/09/2021 | Yeovil Town | - | Chesterfield FC | 0:2 | |
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| 8. Round | 25/09/2021 | Chesterfield FC | - | Torquay United | 2:2 | ||||
| 7. Round | 28/09/2021 | Woking FC | - | Chesterfield FC | 3:1 | |
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| 10. Round | 05/10/2021 | Wrexham AFC | - | Chesterfield FC | 1:1 | ||||
| 12. Round | 23/10/2021 | Chesterfield FC | - | Boreham Wood | 2:1 | ||||
| 13. Round | 26/10/2021 | Chesterfield FC | - | Eastleigh FC | 1:0 | |
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| 14. Round | 30/10/2021 | Dagenham & Redbridge | - | Chesterfield FC | 2:2 | |
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| 15. Round | 13/11/2021 | Chesterfield FC | - | Weymouth FC | 4:0 | ||||
| 16. Round | 20/11/2021 | Solihull Moors | - | Chesterfield FC | 0:2 | ||||
| 17. Round | 23/11/2021 | Chesterfield FC | - | Altrincham FC | 2:2 | ||||
| 20. Round | 11/12/2021 | Grimsby Town | - | Chesterfield FC | 0:1 | ||||
| 18. Round | 18/01/2022 | Maidenhead United | - | Chesterfield FC | 3:2 |
England