| 4. Round | 15/08/1999 | SC Paderborn 07 | - | FK Pirmasens | 1:1 | ||||
| 1. Round | 18/08/1999 | FK Pirmasens | - | Preußen Münster | 0:0 |  |
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| 5. Round | 22/08/1999 | FK Pirmasens | - | SC 07 Idar-Oberstein | 4:1 | ||||
| 2. Round | 25/08/1999 | Eintracht Trier | - | FK Pirmasens | 2:1 | ||||
| 6. Round | 28/08/1999 | SV 07 Elversberg | - | FK Pirmasens | 8:2 | ||||
| 7. Round | 05/09/1999 | FK Pirmasens | - | Rot-Weiss Essen | 2:2 | ||||
| 9. Round | 19/09/1999 | FK Pirmasens | - | 1. FC Saarbrücken | 0:1 | ||||
| 13. Round | 17/10/1999 | FK Pirmasens | - | Sportfreunde Siegen | 1:3 |
Germany