| 1. Round | 09/08/2024 | Chesterfield FC | - | Swindon Town | 1:1 | ||||
| 4. Round | 31/08/2024 | Gillingham FC | - | Chesterfield FC | 1:0 | ||||
| 6. Round | 14/09/2024 | Port Vale FC | - | Chesterfield FC | 1:0 | ||||
| 7. Round | 21/09/2024 | Chesterfield FC | - | Cheltenham Town | 1:1 | ||||
| 18. Round | 03/12/2024 | Milton Keynes Dons | - | Chesterfield FC | 3:0 | ||||
| 19. Round | 07/12/2024 | Chesterfield FC | - | Tranmere Rovers | 3:0 |  |
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| 20. Round | 14/12/2024 | Carlisle United | - | Chesterfield FC | 0:2 | ||||
| 21. Round | 21/12/2024 | Chesterfield FC | - | AFC Wimbledon | 1:0 | ||||
| 22. Round | 26/12/2024 | Fleetwood Town | - | Chesterfield FC | 2:0 |  |
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| 23. Round | 29/12/2024 | Bradford City | - | Chesterfield FC | 2:1 | |
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| 24. Round | 01/01/2025 | Chesterfield FC | - | Milton Keynes Dons | 1:2 | ||||
| 27. Round | 18/01/2025 | Grimsby Town | - | Chesterfield FC | 1:1 | ||||
| 28. Round | 25/01/2025 | Chesterfield FC | - | Port Vale FC | 1:1 | ||||
| 33. Round | 22/02/2025 | Swindon Town | - | Chesterfield FC | 1:0 |
England