| 5. Round | 15/09/2019 | Kickers Offenbach [Youth] | - | FC Augsburg [Youth] | 2:2 | ||||
| 10. Round | 03/11/2019 | SSV Ulm 1846 [Youth] | - | Kickers Offenbach [Youth] | 2:0 |  |
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| 11. Round | 10/11/2019 | Kickers Offenbach [Youth] | - | Bayern München [Youth] | 1:5 | ||||
| 12. Round | 23/11/2019 | SpVgg Greuther Fürth [Youth] | - | Kickers Offenbach [Youth] | 2:2 | ||||
| 13. Round | 01/12/2019 | Kickers Offenbach [Youth] | - | SC Freiburg [Youth] | 1:2 | |
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| 14. Round | 07/12/2019 | Kickers Offenbach [Youth] | - | FC Ingolstadt 04 [Youth] | 2:0 |  |
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| 15. Round | 01/02/2020 | VfB Stuttgart [Youth] | - | Kickers Offenbach [Youth] | 2:0 | ||||
| 16. Round | 07/02/2020 | Eintracht Frankfurt [Youth] | - | Kickers Offenbach [Youth] | 3:2 | |
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| 17. Round | 15/02/2020 | Kickers Offenbach [Youth] | - | Karlsruher SC [Youth] | 3:2 | ||||
| 18. Round | 23/02/2020 | FC Augsburg [Youth] | - | Kickers Offenbach [Youth] | 3:0 | ||||
| 19. Round | 29/02/2020 | Kickers Offenbach [Youth] | - | 1. FC Kaiserslautern [Youth] | 3:0 | |
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| 20. Round | 07/03/2020 | 1. FSV Mainz 05 [Youth] | - | Kickers Offenbach [Youth] | 2:1 |
Germany