| 4. Round | 25/08/2019 | Eintracht Frankfurt [Youth] | - | VfB Stuttgart [Youth] | 2:4 | ||||
| 5. Round | 14/09/2019 | VfB Stuttgart [Youth] | - | SSV Ulm 1846 [Youth] | 3:0 | ||||
| 6. Round | 21/09/2019 | Karlsruher SC [Youth] | - | VfB Stuttgart [Youth] | 1:3 | ||||
| 7. Round | 27/09/2019 | VfB Stuttgart [Youth] | - | Bayern München [Youth] | 1:4 | ||||
| 9. Round | 26/10/2019 | VfB Stuttgart [Youth] | - | SpVgg Greuther Fürth [Youth] | 4:1 | ||||
| 10. Round | 03/11/2019 | 1. FC Kaiserslautern [Youth] | - | VfB Stuttgart [Youth] | 2:3 | ||||
| 11. Round | 09/11/2019 | VfB Stuttgart [Youth] | - | SC Freiburg [Youth] | 2:0 | ||||
| 13. Round | 30/11/2019 | FC Ingolstadt 04 [Youth] | - | VfB Stuttgart [Youth] | 0:1 |  |
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| 14. Round | 07/12/2019 | 1899 Hoffenheim [Youth] | - | VfB Stuttgart [Youth] | 1:3 | ||||
| 16. Round | 08/02/2020 | 1. FC Heidenheim 1846 [Youth] | - | VfB Stuttgart [Youth] | 2:1 |
USA