| 1. Round | 14/07/2019 | TSV 1860 Rosenheim | - | Wacker Burghausen | 4:2 | ||||
| 2. Round | 19/07/2019 | FC Augsburg II | - | TSV 1860 Rosenheim | 1:0 |  |
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| 3. Round | 23/07/2019 | TSV 1860 Rosenheim | - | TSV 1896 Rain | 1:0 | ||||
| 4. Round | 27/07/2019 | FV Illertissen | - | TSV 1860 Rosenheim | 5:3 | ||||
| 9. Round | 30/08/2019 | TSV 1860 Rosenheim | - | SV Schalding-Heining | 3:3 | ||||
| 10. Round | 07/09/2019 | Türkgücü München | - | TSV 1860 Rosenheim | annull. | ||||
| 11. Round | 13/09/2019 | TSV 1860 Rosenheim | - | Viktoria Aschaffenburg | 0:3 | ||||
| 12. Round | 21/09/2019 | VfB Eichstätt | - | TSV 1860 Rosenheim | 1:1 | ||||
| 13. Round | 27/09/2019 | TSV 1860 Rosenheim | - | VfR Garching | 2:1 | ||||
| 14. Round | 05/10/2019 | TSV Aubstadt | - | TSV 1860 Rosenheim | 2:0 | ||||
| 15. Round | 11/10/2019 | TSV 1860 Rosenheim | - | FC Memmingen | 1:1 | ||||
| 21. Round | 23/11/2019 | TSV 1860 Rosenheim | - | FV Illertissen | 1:0 | ||||
| 22. Round | 30/11/2019 | 1. FC Schweinfurt 05 | - | TSV 1860 Rosenheim | 4:3 |
Germany