| 1. Round | 09/08/2024 | Chesterfield FC | - | Swindon Town | 1:1 | ||||
| 5. Round | 07/09/2024 | Chesterfield FC | - | Grimsby Town | 2:1 | ||||
| 6. Round | 14/09/2024 | Port Vale FC | - | Chesterfield FC | 1:0 | ||||
| 7. Round | 21/09/2024 | Chesterfield FC | - | Cheltenham Town | 1:1 |  |
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| 8. Round | 28/09/2024 | Doncaster Rovers | - | Chesterfield FC | 0:3 | ||||
| 15. Round | 09/11/2024 | Chesterfield FC | - | Accrington Stanley | 0:3 | ||||
| 16. Round | 16/11/2024 | Harrogate Town | - | Chesterfield FC | 2:1 | |
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| 17. Round | 23/11/2024 | Chesterfield FC | - | Barrow AFC | 1:0 |
USA