| 5. Round | 31/08/2019 | SV Linx | - | FC 08 Villingen | 1:3 | ||||
| 6. Round | 07/09/2019 | FC 08 Villingen | - | Neckarsulmer Sport-Union | 2:0 | ||||
| 7. Round | 14/09/2019 | FV Ravensburg | - | FC 08 Villingen | 1:1 | ||||
| 8. Round | 21/09/2019 | FC 08 Villingen | - | Freiburger FC | 1:0 | ||||
| 9. Round | 27/09/2019 | FSV 08 Bissingen | - | FC 08 Villingen | 3:3 | ||||
| 10. Round | 06/10/2019 | FC 08 Villingen | - | SV Sandhausen II | 2:1 | ||||
| 11. Round | 12/10/2019 | 1. CfR Pforzheim | - | FC 08 Villingen | 0:1 |  |
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| 12. Round | 19/10/2019 | FC 08 Villingen | - | Stuttgarter Kickers | 2:1 | ||||
| 13. Round | 26/10/2019 | Sportfreunde Dorfmerkingen | - | FC 08 Villingen | 1:1 | ||||
| 14. Round | 02/11/2019 | FC 08 Villingen | - | SGV Freiberg | 3:0 | ||||
| 15. Round | 13/11/2019 | FC Nöttingen | - | FC 08 Villingen | 3:1 | ||||
| 16. Round | 16/11/2019 | FC 08 Villingen | - | SV Oberachern | 0:1 | ||||
| 19. Round | 07/12/2019 | FC 08 Villingen | - | Göppinger SV | 0:2 |  |
Germany