1. Round | 04/08/2018 | Ebbsfleet United | - | Chesterfield FC | 0:1 | ||||
2. Round | 07/08/2018 | Chesterfield FC | - | Aldershot Town | 3:0 | ||||
3. Round | 11/08/2018 | Chesterfield FC | - | Braintree Town | 1:0 | ||||
4. Round | 14/08/2018 | Barrow AFC | - | Chesterfield FC | 3:2 | ||||
5. Round | 18/08/2018 | Salford City | - | Chesterfield FC | 3:2 | ||||
6. Round | 25/08/2018 | Chesterfield FC | - | Barnet FC | 0:1 | ||||
7. Round | 27/08/2018 | Hartlepool United | - | Chesterfield FC | 1:0 | ||||
8. Round | 01/09/2018 | Chesterfield FC | - | Leyton Orient | 0:1 | ||||
9. Round | 04/09/2018 | Boreham Wood | - | Chesterfield FC | 1:0 | ||||
10. Round | 08/09/2018 | Chesterfield FC | - | Dover Athletic | 0:0 | ||||
11. Round | 15/09/2018 | Dagenham & Redbridge | - | Chesterfield FC | 1:1 | ||||
12. Round | 22/09/2018 | Chesterfield FC | - | Gateshead FC | 0:3 | ||||
13. Round | 25/09/2018 | Chesterfield FC | - | Maidenhead United | 1:3 |