5. Round | 17/08/2019 | Barnet FC | - | Chesterfield FC | 2:2 | ||||
6. Round | 24/08/2019 | Chesterfield FC | - | Barrow AFC | 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 | ||||
15. Round | 05/10/2019 | Chesterfield FC | - | Eastleigh FC | 1:2 | ||||
16. Round | 08/10/2019 | AFC Fylde | - | Chesterfield FC | 1:3 | ||||
20. Round | 02/11/2019 | Ebbsfleet United | - | Chesterfield FC | 2:2 | ||||
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 | ||||
19. Round | 10/12/2019 | Chesterfield FC | - | Yeovil Town | 1:2 |