| 18. Round | 19/11/2016 | Fleetwood Town | - | Chesterfield FC | 2:1 | ||||
| 19. Round | 22/11/2016 | Milton Keynes Dons | - | Chesterfield FC | 2:3 | ||||
| 20. Round | 26/11/2016 | Chesterfield FC | - | Bristol Rovers | 3:2 | ||||
| 21. Round | 10/12/2016 | Peterborough United | - | Chesterfield FC | 5:2 | ||||
| 25. Round | 02/01/2017 | Chesterfield FC | - | Milton Keynes Dons | 0:0 | ||||
| 29. Round | 21/02/2017 | Millwall FC | - | Chesterfield FC | 0:0 | ||||
| 46. Round | 30/04/2017 | Sheffield United | - | Chesterfield FC | 3:2 |
England