| 1. Jornada | 04.08.2018 | Ebbsfleet United | - | Chesterfield FC | 0:1 |  |
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| 2. Jornada | 07.08.2018 | Chesterfield FC | - | Aldershot Town | 3:0 | ||||
| 3. Jornada | 11.08.2018 | Chesterfield FC | - | Braintree Town | 1:0 | ||||
| 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 | ||||
| 10. Jornada | 08.09.2018 | Chesterfield FC | - | Dover Athletic | 0:0 |
Inglaterra