| 1. Round | 03/08/2019 | FC Grimma | - | Askania Bernburg | 3:2 | ||||
| 2. Round | 18/08/2019 | Inter Leipzig | - | FC Grimma | 1:2 |  |
|||
| 3. Round | 24/08/2019 | FC Grimma | - | FC Oberlausitz | 4:1 | ||||
| 4. Round | 31/08/2019 | FC Grimma | - | FC Carl Zeiss Jena II | 2:3 | ||||
| 5. Round | 14/09/2019 | FC Grimma | - | FC Einheit Rudolstadt | 0:3 | ||||
| 6. Round | 20/09/2019 | FC Eilenburg | - | FC Grimma | 2:4 | ||||
| 7. Round | 28/09/2019 | FC Grimma | - | VfL 05 Hohenstein-Ernstthal | annull. |  |
|||
| 8. Round | 03/10/2019 | 1. FC Merseburg | - | FC Grimma | 3:1 | ||||
| 18. Round | 29/02/2020 | FC Oberlausitz | - | FC Grimma | 8:1 | ||||
| 19. Round | 06/03/2020 | FC Carl Zeiss Jena II | - | FC Grimma | 2:0 |
Germany