| 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 |  |
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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 | ||||
| 16. Round | 07/11/1999 | SC Verl | - | KFC Uerdingen 05 | 1:1 | |
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| 17. Round | 14/11/1999 | KFC Uerdingen 05 | - | Preußen Münster | 1:2 | ||||
| 18. Round | 28/11/1999 | Bayer Leverkusen II | - | KFC Uerdingen 05 | 0:2 | |
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| 19. Round | 05/12/1999 | KFC Uerdingen 05 | - | SC 07 Idar-Oberstein | 4:0 | |
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| 21. Round | 19/12/1999 | 1. FC Saarbrücken | - | KFC Uerdingen 05 | 2:2 |  |
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| 22. Round | 06/02/2000 | KFC Uerdingen 05 | - | SG Wattenscheid 09 | 2:1 | |
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| 23. Round | 13/02/2000 | Sportfreunde Siegen | - | KFC Uerdingen 05 | 2:2 | ||||
| 24. Round | 15/03/2000 | KFC Uerdingen 05 | - | 1. FC Kaiserslautern II | 1:4 | |
Senegal