| 3. Round | 17/07/1999 | Grasshopper Club Zürich | - | FC Aarau | 4:0 | ||||
| 4. Round | 21/07/1999 | FC Basel 1893 | - | Grasshopper Club Zürich | 1:1 | ||||
| 7. Round | 08/08/1999 | Grasshopper Club Zürich | - | FC Lugano | 2:1 | ||||
| 8. Round | 15/08/1999 | Grasshopper Club Zürich | - | FC St. Gallen | 2:2 | ||||
| 9. Round | 22/08/1999 | SR Delémont | - | Grasshopper Club Zürich | 2:1 | ||||
| 10. Round | 29/08/1999 | Grasshopper Club Zürich | - | Servette FC | 4:2 | ||||
| 11. Round | 12/09/1999 | FC Luzern | - | Grasshopper Club Zürich | 2:0 | ||||
| 12. Round | 20/09/1999 | Lausanne Sports | - | Grasshopper Club Zürich | 3:3 | ||||
| 14. Round | 03/10/1999 | FC Aarau | - | Grasshopper Club Zürich | 2:1 | ||||
| 19. Round | 01/12/1999 | FC St. Gallen | - | Grasshopper Club Zürich | 2:1 | ||||
| 21. Round | 05/12/1999 | Servette FC | - | Grasshopper Club Zürich | 2:1 | ||||
| 22. Round | 12/12/1999 | Grasshopper Club Zürich | - | FC Luzern | 2:0 |
Switzerland