| 1. Round | 26/07/2019 | Rot-Weiss Essen | - | Borussia Dortmund II | 2:1 |  |
|||
| 2. Round | 04/08/2019 | VfB Homberg | - | Rot-Weiss Essen | 1:2 | ||||
| 3. Round | 11/08/2019 | Rot-Weiss Essen | - | 1. FC Köln II | 2:1 | ||||
| 4. Round | 17/08/2019 | SV Rödinghausen | - | Rot-Weiss Essen | 1:1 | ||||
| 5. Round | 23/08/2019 | Rot-Weiss Essen | - | SG Wattenscheid 09 | annull. | ||||
| 8. Round | 13/09/2019 | SV Lippstadt 08 | - | Rot-Weiss Essen | 2:4 | ||||
| 9. Round | 20/09/2019 | Rot-Weiss Essen | - | Bonner SC | 4:1 | ||||
| 11. Round | 29/09/2019 | Rot-Weiss Essen | - | SC Verl | 1:4 | ||||
| 14. Round | 19/10/2019 | SV Bergisch Gladbach 09 | - | Rot-Weiss Essen | 1:2 |  |
|||
| 15. Round | 26/10/2019 | Fortuna Düsseldorf II | - | Rot-Weiss Essen | 0:1 | ||||
| 16. Round | 02/11/2019 | Rot-Weiss Essen | - | Sportfreunde Lotte | 4:1 | ||||
| 18. Round | 16/11/2019 | Rot-Weiss Essen | - | Alemannia Aachen | 3:0 | ||||
| 10. Round | 23/11/2019 | FC Schalke 04 II | - | Rot-Weiss Essen | 0:0 | ||||
| 20. Round | 08/12/2019 | Borussia Dortmund II | - | Rot-Weiss Essen | 0:1 | ||||
| 21. Round | 13/12/2019 | Rot-Weiss Essen | - | VfB Homberg | 0:2 |
Germany