| 1. Jornada | 04.08.2018 | Ebbsfleet United | - | Chesterfield FC | 0:1 | ||||
| 2. Jornada | 07.08.2018 | Chesterfield FC | - | Aldershot Town | 3:0 | ||||
| 3. Jornada | 11.08.2018 | Chesterfield FC | - | Braintree Town | 1:0 | ||||
| 4. Jornada | 14.08.2018 | Barrow AFC | - | Chesterfield FC | 3:2 | ||||
| 5. Jornada | 18.08.2018 | Salford City | - | Chesterfield FC | 3:2 | ||||
| 6. Jornada | 25.08.2018 | Chesterfield FC | - | Barnet FC | 0:1 | ||||
| 7. Jornada | 27.08.2018 | Hartlepool United | - | Chesterfield FC | 1:0 | ||||
| 8. Jornada | 01.09.2018 | Chesterfield FC | - | Leyton Orient | 0:1 | ||||
| 9. Jornada | 04.09.2018 | Boreham Wood | - | Chesterfield FC | 1:0 |  |
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| 10. Jornada | 08.09.2018 | Chesterfield FC | - | Dover Athletic | 0:0 | |
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| 12. Jornada | 22.09.2018 | Chesterfield FC | - | Gateshead FC | 0:3 | ||||
| 13. Jornada | 25.09.2018 | Chesterfield FC | - | Maidenhead United | 1:3 | ||||
| 26. Jornada | 26.12.2018 | Chesterfield FC | - | Solihull Moors | 0:4 |
Inglaterra