| 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 |  |
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| 3. Jornada | 11.08.2018 | Chesterfield FC | - | Braintree Town | 1:0 | |
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| 4. Jornada | 14.08.2018 | Barrow AFC | - | Chesterfield FC | 3:2 | |
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| 5. Jornada | 18.08.2018 | Salford City | - | Chesterfield FC | 3:2 | |
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| 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 | ||||
| 11. Jornada | 15.09.2018 | Dagenham & Redbridge | - | Chesterfield FC | 1:1 | ||||
| 12. Jornada | 22.09.2018 | Chesterfield FC | - | Gateshead FC | 0:3 |  |
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| 16. Jornada | 13.10.2018 | Halifax Town | - | Chesterfield FC | 1:1 | ||||
| 17. Jornada | 27.10.2018 | Chesterfield FC | - | Wrexham AFC | 1:1 | ||||
| 18. Jornada | 30.10.2018 | Sutton United | - | Chesterfield FC | 1:1 | ||||
| 19. Jornada | 03.11.2018 | Harrogate Town | - | Chesterfield FC | 1:1 | |
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| 22. Jornada | 27.11.2018 | Chesterfield FC | - | Bromley FC | 1:1 | |
Jamaica
Inglaterra