1. Round | 03/08/2019 | Chesterfield FC | - | Dover Athletic | 1:2 | ||||
2. Round | 06/08/2019 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
4. Round | 13/08/2019 | Chesterfield FC | - | Woking FC | 1:2 | ||||
7. Round | 26/08/2019 | Stockport County | - | Chesterfield FC | 2:0 | ||||
9. Round | 03/09/2019 | Chesterfield FC | - | Halifax Town | 2:3 | ||||
10. Round | 07/09/2019 | Bromley FC | - | Chesterfield FC | 2:1 | ||||
12. Round | 21/09/2019 | Sutton United | - | Chesterfield FC | 4:0 | ||||
26. Round | 21/12/2019 | Torquay United | - | Chesterfield FC | 0:3 | ||||
27. Round | 26/12/2019 | Chesterfield FC | - | Solihull Moors | 2:2 | ||||
28. Round | 28/12/2019 | Halifax Town | - | Chesterfield FC | 1:0 | ||||
29. Round | 01/01/2020 | Solihull Moors | - | Chesterfield FC | 3:0 | ||||
30. Round | 04/01/2020 | Chesterfield FC | - | Sutton United | 1:0 | ||||
31. Round | 18/01/2020 | Eastleigh FC | - | Chesterfield FC | 0:2 | ||||
33. Round | 01/02/2020 | Notts County | - | Chesterfield FC | 3:0 |