9. Round | 04/09/2018 | Boreham Wood | - | Chesterfield FC | 1:0 | ||||
15. Round | 06/10/2018 | Chesterfield FC | - | AFC Fylde | 0:0 | ||||
17. Round | 27/10/2018 | Chesterfield FC | - | Wrexham AFC | 1:1 | ||||
18. Round | 30/10/2018 | Sutton United | - | Chesterfield FC | 1:1 | ||||
20. Round | 17/11/2018 | Chesterfield FC | - | Havant & Waterlooville | 0:0 | ||||
21. Round | 24/11/2018 | Eastleigh FC | - | Chesterfield FC | 1:1 | ||||
22. Round | 27/11/2018 | Chesterfield FC | - | Bromley FC | 1:1 | ||||
24. Round | 08/12/2018 | Chesterfield FC | - | Salford City | 2:0 | ||||
25. Round | 22/12/2018 | Leyton Orient | - | Chesterfield FC | 3:1 | ||||
26. Round | 26/12/2018 | Chesterfield FC | - | Solihull Moors | 0:4 | ||||
27. Round | 29/12/2018 | Chesterfield FC | - | Hartlepool United | 1:1 |