| 1. Jornada | 03.08.2019 | Chesterfield FC | - | Dover Athletic | 1:2 | ||||
| 2. Jornada | 06.08.2019 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
| 4. Jornada | 13.08.2019 | Chesterfield FC | - | Woking FC | 1:2 | ||||
| 7. Jornada | 26.08.2019 | Stockport County | - | Chesterfield FC | 2:0 | ||||
| 9. Jornada | 03.09.2019 | Chesterfield FC | - | Halifax Town | 2:3 | ||||
| 10. Jornada | 07.09.2019 | Bromley FC | - | Chesterfield FC | 2:1 | ||||
| 12. Jornada | 21.09.2019 | Sutton United | - | Chesterfield FC | 4:0 | ||||
| 26. Jornada | 21.12.2019 | Torquay United | - | Chesterfield FC | 0:3 |  |
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| 27. Jornada | 26.12.2019 | Chesterfield FC | - | Solihull Moors | 2:2 | |
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| 28. Jornada | 28.12.2019 | Halifax Town | - | Chesterfield FC | 1:0 | ||||
| 29. Jornada | 01.01.2020 | Solihull Moors | - | Chesterfield FC | 3:0 |  |
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| 30. Jornada | 04.01.2020 | Chesterfield FC | - | Sutton United | 1:0 | ||||
| 31. Jornada | 18.01.2020 | Eastleigh FC | - | Chesterfield FC | 0:2 | ||||
| 33. Jornada | 01.02.2020 | Notts County | - | Chesterfield FC | 3:0 |
Escocia
Inglaterra