| 1. Round | 01/08/1999 | Rot-Weiss Essen | - | KFC Uerdingen 05 | 1:0 | ||||
| 3. Round | 11/08/1999 | SG Wattenscheid 09 | - | KFC Uerdingen 05 | 1:2 |  |
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| 4. Round | 15/08/1999 | KFC Uerdingen 05 | - | Sportfreunde Siegen | 2:1 | ||||
| 5. Round | 21/08/1999 | 1. FC Kaiserslautern II | - | KFC Uerdingen 05 | 1:1 |  |
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| 2. Round | 25/08/1999 | KFC Uerdingen 05 | - | 1. FC Saarbrücken | 1:3 | ||||
| 7. Round | 05/09/1999 | LR Ahlen | - | KFC Uerdingen 05 | 3:2 | |
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| 8. Round | 12/09/1999 | KFC Uerdingen 05 | - | Eintracht Trier | 3:1 | ||||
| 9. Round | 19/09/1999 | SC Paderborn 07 | - | KFC Uerdingen 05 | 1:0 | ||||
| 10. Round | 26/09/1999 | KFC Uerdingen 05 | - | SV 07 Elversberg | 1:2 | ||||
| 11. Round | 03/10/1999 | Borussia Dortmund II | - | KFC Uerdingen 05 | 3:0 | ||||
| 12. Round | 10/10/1999 | KFC Uerdingen 05 | - | VfL Bochum II | 3:3 | ||||
| 13. Round | 16/10/1999 | Fortuna Düsseldorf | - | KFC Uerdingen 05 | 1:1 | |
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| 14. Round | 24/10/1999 | KFC Uerdingen 05 | - | FK Pirmasens | 1:2 | ||||
| 15. Round | 31/10/1999 | KFC Uerdingen 05 | - | FSV Salmrohr | 2:0 | ||||
| 17. Round | 14/11/1999 | KFC Uerdingen 05 | - | Preußen Münster | 1:2 |
Czech Republic