| 2. Round | 10/08/2003 | VfL Osnabrück | - | Karlsruher SC | 1:2 | ||||
| 3. Round | 17/08/2003 | Wacker Burghausen | - | VfL Osnabrück | 4:1 | ||||
| 4. Round | 24/08/2003 | VfL Osnabrück | - | 1. FSV Mainz 05 | 2:2 | ||||
| 5. Round | 14/09/2003 | Energie Cottbus | - | VfL Osnabrück | 3:0 | ||||
| 6. Round | 21/09/2003 | VfL Osnabrück | - | Erzgebirge Aue | 0:1 | ||||
| 7. Round | 28/09/2003 | SpVgg Greuther Fürth | - | VfL Osnabrück | 1:1 | ||||
| 8. Round | 03/10/2003 | VfL Osnabrück | - | MSV Duisburg | 2:2 | ||||
| 10. Round | 26/10/2003 | VfL Osnabrück | - | SpVgg Unterhaching | 2:1 | ||||
| 12. Round | 07/11/2003 | VfL Osnabrück | - | Eintracht Trier | 3:0 | ||||
| 13. Round | 21/11/2003 | 1. FC Union Berlin | - | VfL Osnabrück | 2:0 |
North Macedonia