| 1. Round | 11/08/2019 | Arminia Bielefeld [Youth] | - | Rot-Weiß Oberhausen [Youth] | 1:2 | ||||
| 2. Round | 17/08/2019 | FC Schalke 04 [Youth] | - | Arminia Bielefeld [Youth] | 2:1 | ||||
| 3. Round | 21/08/2019 | Arminia Bielefeld [Youth] | - | Preußen Münster [Youth] | 3:1 | ||||
| 7. Round | 28/09/2019 | Arminia Bielefeld [Youth] | - | VfL Bochum [Youth] | 2:1 |  |
|||
| 12. Round | 23/11/2019 | Arminia Bielefeld [Youth] | - | Viktoria Köln [Youth] | 2:1 | ||||
| 13. Round | 30/11/2019 | Bayer Leverkusen [Youth] | - | Arminia Bielefeld [Youth] | 3:0 | ||||
| 14. Round | 08/12/2019 | Rot-Weiß Oberhausen [Youth] | - | Arminia Bielefeld [Youth] | 2:2 | ||||
| 16. Round | 09/02/2020 | Preußen Münster [Youth] | - | Arminia Bielefeld [Youth] | 1:2 | ||||
| 18. Round | 22/02/2020 | Fortuna Düsseldorf [Youth] | - | Arminia Bielefeld [Youth] | 5:0 | ||||
| 19. Round | 29/02/2020 | Arminia Bielefeld [Youth] | - | Alemannia Aachen [Youth] | 6:3 | ||||
| 20. Round | 07/03/2020 | VfL Bochum [Youth] | - | Arminia Bielefeld [Youth] | 3:2 |
Germany