14. Round | 28/09/2019 | Chesterfield FC | - | Aldershot Town | 2:1 | ||||
15. Round | 05/10/2019 | Chesterfield FC | - | Eastleigh FC | 1:2 | ||||
16. Round | 08/10/2019 | AFC Fylde | - | Chesterfield FC | 1:3 | ||||
18. Round | 26/10/2019 | Chesterfield FC | - | Notts County | 1:0 | ||||
20. Round | 02/11/2019 | Ebbsfleet United | - | Chesterfield FC | 2:2 |