| 4. Round | 26/08/2019 | FC St. Pauli | - | Holstein Kiel | 2:1 | ||||
| 6. Round | 14/09/2019 | 1. FC Heidenheim 1846 | - | Holstein Kiel | 3:0 | ||||
| 7. Round | 20/09/2019 | Holstein Kiel | - | Hannover 96 | 1:2 | ||||
| 8. Round | 29/09/2019 | SpVgg Greuther Fürth | - | Holstein Kiel | 0:3 |  |
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| 9. Round | 06/10/2019 | Holstein Kiel | - | Jahn Regensburg | 1:2 | ||||
| 14. Round | 23/11/2019 | SV Wehen Wiesbaden | - | Holstein Kiel | 3:6 | ||||
| 15. Round | 30/11/2019 | Dynamo Dresden | - | Holstein Kiel | 1:2 | ||||
| 34. Round | 28/06/2020 | Holstein Kiel | - | 1. FC Nürnberg | 1:1 |
Switzerland