| 1. Round | 09/08/2024 | Chesterfield FC | - | Swindon Town | 1:1 | ||||
| 2. Round | 17/08/2024 | Crewe Alexandra | - | Chesterfield FC | 0:5 | ||||
| 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 | ||||
| 6. Round | 14/09/2024 | Port Vale FC | - | Chesterfield FC | 1:0 | ||||
| 9. Round | 01/10/2024 | Bromley FC | - | Chesterfield FC | 2:2 | ||||
| 11. Round | 12/10/2024 | Chesterfield FC | - | Notts County | 2:2 | ||||
| 12. Round | 18/10/2024 | Newport County | - | Chesterfield FC | 0:3 | ||||
| 13. Round | 22/10/2024 | Chesterfield FC | - | Colchester United | 1:1 | ||||
| 15. Round | 09/11/2024 | Chesterfield FC | - | Accrington Stanley | 0:3 | ||||
| 34. Round | 01/03/2025 | Chesterfield FC | - | Crewe Alexandra | 1:3 | ||||
| 39. Round | 29/03/2025 | Barrow AFC | - | Chesterfield FC | 0:1 |  |
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| 40. Round | 01/04/2025 | Chesterfield FC | - | Carlisle United | 2:1 | ||||
| 41. Round | 05/04/2025 | Tranmere Rovers | - | Chesterfield FC | 4:0 | ||||
| 45. Round | 26/04/2025 | Chesterfield FC | - | Morecambe FC | 4:1 | ||||
| 46. Round | 03/05/2025 | Accrington Stanley | - | Chesterfield FC | 0:1 |
England