| 2. Round | 06/08/2019 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
| 3. Round | 10/08/2019 | Boreham Wood | - | Chesterfield FC | 2:2 | ||||
| 4. Round | 13/08/2019 | Chesterfield FC | - | Woking FC | 1:2 | ||||
| 13. Round | 24/09/2019 | Hartlepool United | - | Chesterfield FC | 1:1 | ||||
| 14. Round | 28/09/2019 | Chesterfield FC | - | Aldershot Town | 2:1 | ||||
| 15. Round | 05/10/2019 | Chesterfield FC | - | Eastleigh FC | 1:2 | ||||
| 16. Round | 08/10/2019 | AFC Fylde | - | Chesterfield FC | 1:3 | ||||
| 17. Round | 15/10/2019 | Wrexham AFC | - | Chesterfield FC | 0:1 | ||||
| 23. Round | 26/11/2019 | Chesterfield FC | - | Hartlepool United | 1:5 | ||||
| 30. Round | 04/01/2020 | Chesterfield FC | - | Sutton United | 1:0 |  |
|||
| 31. Round | 18/01/2020 | Eastleigh FC | - | Chesterfield FC | 0:2 | ||||
| 32. Round | 25/01/2020 | Chesterfield FC | - | AFC Fylde | 1:1 | ||||
| 33. Round | 01/02/2020 | Notts County | - | Chesterfield FC | 3:0 |
England