2. Round | 06/08/2019 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
3. Round | 10/08/2019 | Boreham Wood | - | Chesterfield FC | 2:2 | ||||
7. Round | 26/08/2019 | Stockport County | - | Chesterfield FC | 2:0 | ||||
8. Round | 31/08/2019 | Chesterfield FC | - | Dagenham & Redbridge | 1:1 | ||||
9. Round | 03/09/2019 | Chesterfield FC | - | Halifax Town | 2:3 | ||||
10. Round | 07/09/2019 | Bromley FC | - | Chesterfield FC | 2:1 | ||||
11. Round | 14/09/2019 | Chesterfield FC | - | Torquay United | 1:0 | ||||
21. Round | 16/11/2019 | Chesterfield FC | - | Chorley FC | 2:3 | ||||
22. Round | 23/11/2019 | Harrogate Town | - | Chesterfield FC | 3:1 | ||||
23. Round | 26/11/2019 | Chesterfield FC | - | Hartlepool United | 1:5 | ||||
24. Round | 30/11/2019 | Aldershot Town | - | Chesterfield FC | 2:2 | ||||
25. Round | 07/12/2019 | Chesterfield FC | - | Bromley FC | 1:2 | ||||
19. Round | 10/12/2019 | Chesterfield FC | - | Yeovil Town | 1:2 | ||||
26. Round | 21/12/2019 | Torquay United | - | Chesterfield FC | 0:3 | ||||
27. Round | 26/12/2019 | Chesterfield FC | - | Solihull Moors | 2:2 |