| 2. Round | 08/08/1999 | SC Paderborn 07 | - | LR Ahlen | 0:0 | ||||
| 4. Round | 15/08/1999 | Borussia Dortmund II | - | LR Ahlen | 1:3 | ||||
| 5. Round | 22/08/1999 | LR Ahlen | - | VfL Bochum II | 1:1 | ||||
| 7. Round | 05/09/1999 | LR Ahlen | - | KFC Uerdingen 05 | 3:2 |  |
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| 8. Round | 11/09/1999 | FSV Salmrohr | - | LR Ahlen | 0:4 | |
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| 9. Round | 19/09/1999 | LR Ahlen | - | SC Verl | 2:2 | ||||
| 10. Round | 26/09/1999 | Preußen Münster | - | LR Ahlen | 0:2 | ||||
| 11. Round | 03/10/1999 | LR Ahlen | - | Bayer Leverkusen II | 0:0 | ||||
| 12. Round | 10/10/1999 | SC 07 Idar-Oberstein | - | LR Ahlen | 1:4 | ||||
| 13. Round | 17/10/1999 | LR Ahlen | - | Rot-Weiss Essen | 3:3 | ||||
| 14. Round | 23/10/1999 | 1. FC Saarbrücken | - | LR Ahlen | 2:1 | ||||
| 16. Round | 07/11/1999 | Sportfreunde Siegen | - | LR Ahlen | 0:0 | ||||
| 20. Round | 11/12/1999 | Eintracht Trier | - | LR Ahlen | 0:4 | ||||
| 21. Round | 18/12/1999 | LR Ahlen | - | SC Paderborn 07 | 3:1 |
???
Spain