| 2. Jornada | 06.08.2019 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
| 3. Jornada | 10.08.2019 | Boreham Wood | - | Chesterfield FC | 2:2 | ||||
| 4. Jornada | 13.08.2019 | Chesterfield FC | - | Woking FC | 1:2 | ||||
| 13. Jornada | 24.09.2019 | Hartlepool United | - | Chesterfield FC | 1:1 | ||||
| 14. Jornada | 28.09.2019 | Chesterfield FC | - | Aldershot Town | 2:1 | ||||
| 15. Jornada | 05.10.2019 | Chesterfield FC | - | Eastleigh FC | 1:2 | ||||
| 16. Jornada | 08.10.2019 | AFC Fylde | - | Chesterfield FC | 1:3 | ||||
| 17. Jornada | 15.10.2019 | Wrexham AFC | - | Chesterfield FC | 0:1 | ||||
| 23. Jornada | 26.11.2019 | Chesterfield FC | - | Hartlepool United | 1:5 | ||||
| 30. Jornada | 04.01.2020 | Chesterfield FC | - | Sutton United | 1:0 |  |
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| 31. Jornada | 18.01.2020 | Eastleigh FC | - | Chesterfield FC | 0:2 | ||||
| 32. Jornada | 25.01.2020 | Chesterfield FC | - | AFC Fylde | 1:1 | ||||
| 33. Jornada | 01.02.2020 | Notts County | - | Chesterfield FC | 3:0 |
Inglaterra