| 2. Round | 18/08/1999 | Fortuna Düsseldorf | - | SG Wattenscheid 09 | 3:1 | ||||
| 5. Round | 22/08/1999 | SG Wattenscheid 09 | - | SC Verl | 2:2 | ||||
| 6. Round | 29/08/1999 | Preußen Münster | - | SG Wattenscheid 09 | 2:3 | ||||
| 7. Round | 05/09/1999 | SG Wattenscheid 09 | - | Bayer Leverkusen II | 3:1 | ||||
| 8. Round | 11/09/1999 | SC 07 Idar-Oberstein | - | SG Wattenscheid 09 | 2:4 | ||||
| 9. Round | 19/09/1999 | SG Wattenscheid 09 | - | Rot-Weiss Essen | 0:2 |  |
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| 10. Round | 26/09/1999 | 1. FC Saarbrücken | - | SG Wattenscheid 09 | 1:1 | ||||
| 11. Round | 02/10/1999 | FK Pirmasens | - | SG Wattenscheid 09 | 2:3 | ||||
| 12. Round | 10/10/1999 | SG Wattenscheid 09 | - | Sportfreunde Siegen | 2:2 |
Turkey