| 2. Round | 17/08/2024 | Crewe Alexandra | - | Chesterfield FC | 0:5 | ||||
| 3. Round | 24/08/2024 | Chesterfield FC | - | Salford City | 1:1 | ||||
| 19. Round | 07/12/2024 | Chesterfield FC | - | Tranmere Rovers | 3:0 | ||||
| 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 | ||||
| 23. Round | 29/12/2024 | Bradford City | - | Chesterfield FC | 2:1 | ||||
| 24. Round | 01/01/2025 | Chesterfield FC | - | Milton Keynes Dons | 1:2 | ||||
| 27. Round | 18/01/2025 | Grimsby Town | - | Chesterfield FC | 1:1 | ||||
| 35. Round | 04/03/2025 | Colchester United | - | Chesterfield FC | 1:0 | ||||
| 37. Round | 15/03/2025 | Notts County | - | Chesterfield FC | 1:2 |
England