| 3. Round | 11/08/1999 | SG Wattenscheid 09 | - | KFC Uerdingen 05 | 1:2 | ||||
| 4. Round | 15/08/1999 | FSV Salmrohr | - | SG Wattenscheid 09 | 1:4 |  |
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| 2. Round | 18/08/1999 | Fortuna Düsseldorf | - | SG Wattenscheid 09 | 3:1 | |
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| 5. Round | 22/08/1999 | SG Wattenscheid 09 | - | SC Verl | 2:2 | ||||
| 6. Round | 29/08/1999 | Preußen Münster | - | SG Wattenscheid 09 | 2:3 | ||||
| 9. Round | 19/09/1999 | SG Wattenscheid 09 | - | Rot-Weiss Essen | 0:2 | ||||
| 18. Round | 27/11/1999 | SG Wattenscheid 09 | - | SV 07 Elversberg | 1:2 | ||||
| 20. Round | 11/12/1999 | VfL Bochum II | - | SG Wattenscheid 09 | 1:3 | ||||
| 24. Round | 05/04/2000 | SC Verl | - | SG Wattenscheid 09 | 1:2 | ||||
| 31. Round | 09/04/2000 | Sportfreunde Siegen | - | SG Wattenscheid 09 | 0:3 | ||||
| 32. Round | 16/04/2000 | SG Wattenscheid 09 | - | 1. FC Kaiserslautern II | 1:1 | ||||
| 34. Round | 30/04/2000 | SG Wattenscheid 09 | - | LR Ahlen | 4:1 | ||||
| 35. Round | 07/05/2000 | Eintracht Trier | - | SG Wattenscheid 09 | 3:2 | |
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| 36. Round | 14/05/2000 | SG Wattenscheid 09 | - | SC Paderborn 07 | 2:0 | ||||
| 37. Round | 20/05/2000 | SV 07 Elversberg | - | SG Wattenscheid 09 | 1:2 |
Germany