| 7. Round | 05/09/1999 | SC Paderborn 07 | - | VfL Bochum II | 1:1 | ||||
| 16. Round | 07/11/1999 | 1. FC Saarbrücken | - | SC Paderborn 07 | 3:0 | ||||
| 18. Round | 28/11/1999 | Sportfreunde Siegen | - | SC Paderborn 07 | 1:0 | ||||
| 19. Round | 05/12/1999 | SC Paderborn 07 | - | 1. FC Kaiserslautern II | 0:1 | ||||
| 37. Round | 22/05/2000 | SC Paderborn 07 | - | Sportfreunde Siegen | 2:1 |
Mauritius