| 1. Round | 07/07/1999 | Grasshopper Club Zürich | - | Lausanne Sports | 1:1 |  |
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| 2. Round | 11/07/1999 | FC Zürich | - | Grasshopper Club Zürich | 0:0 | ||||
| 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 | ||||
| 5. Round | 24/07/1999 | Grasshopper Club Zürich | - | Neuchâtel Xamax FC | 4:0 | ||||
| 6. Round | 31/07/1999 | Yverdon Sport FC | - | Grasshopper Club Zürich | 2:0 | ||||
| 7. Round | 08/08/1999 | Grasshopper Club Zürich | - | FC Lugano | 2:1 | ||||
| 15. Round | 17/10/1999 | Grasshopper Club Zürich | - | FC Basel 1893 | 1:1 | ||||
| 16. Round | 24/10/1999 | Neuchâtel Xamax FC | - | Grasshopper Club Zürich | 0:1 | ||||
| 17. Round | 31/10/1999 | Grasshopper Club Zürich | - | Yverdon Sport FC | 0:0 | |
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| 18. Round | 07/11/1999 | FC Lugano | - | Grasshopper Club Zürich | 1:5 |
Switzerland
Austria