| 2. Round | 13/08/2016 | Chesterfield FC | - | Swindon Town | 3:1 | ||||
| 30. Round | 04/02/2017 | Chesterfield FC | - | Oldham Athletic | 0:1 | ||||
| 31. Round | 11/02/2017 | Northampton Town | - | Chesterfield FC | 3:1 | ||||
| 33. Round | 18/02/2017 | Chesterfield FC | - | Bury FC | 1:2 | ||||
| 29. Round | 21/02/2017 | Millwall FC | - | Chesterfield FC | 0:0 | ||||
| 34. Round | 25/02/2017 | Chesterfield FC | - | Oxford United | 0:4 | ||||
| 36. Round | 04/03/2017 | Swindon Town | - | Chesterfield FC | 0:1 |  |
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| 35. Round | 07/03/2017 | Walsall FC | - | Chesterfield FC | 1:0 | ||||
| 37. Round | 11/03/2017 | Chesterfield FC | - | Shrewsbury Town | 1:1 | ||||
| 38. Round | 14/03/2017 | Chesterfield FC | - | Peterborough United | 3:3 | ||||
| 39. Round | 18/03/2017 | Bristol Rovers | - | Chesterfield FC | 2:1 | ||||
| 42. Round | 08/04/2017 | Chesterfield FC | - | Port Vale FC | 1:0 | ||||
| 43. Round | 14/04/2017 | Chesterfield FC | - | Southend United | 0:4 | ||||
| 44. Round | 17/04/2017 | Scunthorpe United | - | Chesterfield FC | 3:1 |
England