| 7. Ronde | 02.09.2023 | Aldershot Town | - | Chesterfield FC | 3:4 | ||||
| 8. Ronde | 09.09.2023 | Chesterfield FC | - | Dagenham & Redbridge | 3:1 | ||||
| 9. Ronde | 16.09.2023 | Ebbsfleet United | - | Chesterfield FC | 0:1 | ||||
| 10. Ronde | 19.09.2023 | Chesterfield FC | - | Halifax Town | 3:2 | ||||
| 11. Ronde | 23.09.2023 | Chesterfield FC | - | Wealdstone FC | 3:2 | ||||
| 12. Ronde | 26.09.2023 | Rochdale AFC | - | Chesterfield FC | 1:2 |  |
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| 13. Ronde | 30.09.2023 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
| 18. Ronde | 28.10.2023 | Kidderminster Harriers | - | Chesterfield FC | 1:3 | |
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| 21. Ronde | 21.11.2023 | Woking FC | - | Chesterfield FC | 0:2 | ||||
| 22. Ronde | 25.11.2023 | Chesterfield FC | - | Eastleigh FC | 3:2 | ||||
| 24. Ronde | 16.12.2023 | Hartlepool United | - | Chesterfield FC | 0:1 | ||||
| 25. Ronde | 23.12.2023 | Chesterfield FC | - | Aldershot Town | 4:1 | ||||
| 26. Ronde | 26.12.2023 | Solihull Moors | - | Chesterfield FC | 2:0 | ||||
| 27. Ronde | 01.01.2024 | Chesterfield FC | - | Solihull Moors | 3:2 | ||||
| 43. Ronde | 01.04.2024 | Chesterfield FC | - | Kidderminster Harriers | 1:3 | ||||
| 46. Ronde | 20.04.2024 | Chesterfield FC | - | Maidenhead United | 3:2 |
Engeland
Jamaica