| 1. Round | 03/08/2019 | Chesterfield FC | - | Dover Athletic | 1:2 |  |
 |
||
| 2. Round | 06/08/2019 | Dover Athletic | - | Dagenham & Redbridge | 1:2 | |
|||
| 3. Round | 10/08/2019 | Dover Athletic | - | Wrexham AFC | 2:1 | ||||
| 4. Round | 13/08/2019 | Barnet FC | - | Dover Athletic | 0:1 | ||||
| 5. Round | 17/08/2019 | Dover Athletic | - | Torquay United | 1:2 | |
|||
| 6. Round | 24/08/2019 | Sutton United | - | Dover Athletic | 1:2 | ||||
| 7. Round | 26/08/2019 | Dover Athletic | - | Woking FC | 1:2 | ||||
| 9. Round | 03/09/2019 | Dover Athletic | - | Ebbsfleet United | 1:1 | ||||
| 10. Round | 07/09/2019 | Boreham Wood | - | Dover Athletic | 3:1 | ||||
| 11. Round | 14/09/2019 | Dover Athletic | - | Chorley FC | 1:1 |
England