| 2. Round | 17/08/2024 | Crewe Alexandra | - | Chesterfield FC | 0:5 |  |
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| 3. Round | 24/08/2024 | Chesterfield FC | - | Salford City | 1:1 | ||||
| 4. Round | 31/08/2024 | Gillingham FC | - | Chesterfield FC | 1:0 | ||||
| 5. Round | 07/09/2024 | Chesterfield FC | - | Grimsby Town | 2:1 | ||||
| 9. Round | 01/10/2024 | Bromley FC | - | Chesterfield FC | 2:2 | ||||
| 10. Round | 05/10/2024 | Chesterfield FC | - | Walsall FC | 2:2 | ||||
| 12. Round | 18/10/2024 | Newport County | - | Chesterfield FC | 0:3 | ||||
| 13. Round | 22/10/2024 | Chesterfield FC | - | Colchester United | 1:1 | ||||
| 14. Round | 26/10/2024 | Morecambe FC | - | Chesterfield FC | 2:5 |
England
Jamaica