| 1. Round | 12/08/2018 | FCE Rheine | - | SC Paderborn 07 II | 5:3 |  |
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| 2. Round | 19/08/2018 | SC Paderborn 07 II | - | 1. FC Gievenbeck | 3:0 | |
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| 3. Round | 25/08/2018 | SC Paderborn 07 II | - | FC Schalke 04 II | 1:4 | ||||
| 4. Round | 02/09/2018 | TuS Haltern | - | SC Paderborn 07 II | 2:0 |  |
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| 5. Round | 09/09/2018 | SC Paderborn 07 II | - | TuS Ennepetal | 2:2 | ||||
| 6. Round | 16/09/2018 | Hammer SpVg | - | SC Paderborn 07 II | 4:2 | |
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| 7. Round | 23/09/2018 | SC Paderborn 07 II | - | FC Brünninghausen | 1:0 | |
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| 8. Round | 30/09/2018 | TSG Sprockhövel | - | SC Paderborn 07 II | 2:4 | |
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| 11. Round | 21/10/2018 | SC Paderborn 07 II | - | Sportfreunde Siegen | 3:3 | |
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| 12. Round | 28/10/2018 | Holzwickeder SC | - | SC Paderborn 07 II | 1:1 | |
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| 13. Round | 04/11/2018 | SC Paderborn 07 II | - | FC Gütersloh | 2:0 | ||||
| 14. Round | 09/11/2018 | Rot Weiss Ahlen | - | SC Paderborn 07 II | 1:0 | ||||
| 15. Round | 18/11/2018 | SC Paderborn 07 II | - | Westfalia Rhynern | 2:3 | ||||
| 16. Round | 02/12/2018 | ASC 09 Dortmund | - | SC Paderborn 07 II | 3:1 | ||||
| 17. Round | 08/12/2018 | SC Paderborn 07 II | - | Westfalia Herne | 0:2 | ||||
| 18. Round | 14/12/2018 | SC Paderborn 07 II | - | FCE Rheine | 8:1 | |
Germany