| 1. Round | 03/03/1999 | Neuchâtel Xamax FC | - | Grasshopper Club Zürich | 1:1 | ||||
| 2. Round | 07/03/1999 | Grasshopper Club Zürich | - | FC Luzern | 4:0 | ||||
| 3. Round | 13/03/1999 | FC Zürich | - | Grasshopper Club Zürich | 0:1 |  |
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| 4. Round | 21/03/1999 | Grasshopper Club Zürich | - | Servette FC | 0:1 | ||||
| 7. Round | 16/04/1999 | Lausanne Sports | - | Grasshopper Club Zürich | 2:3 | ||||
| 8. Round | 23/04/1999 | Grasshopper Club Zürich | - | Lausanne Sports | 5:0 | |
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| 9. Round | 02/05/1999 | Grasshopper Club Zürich | - | FC St. Gallen | 4:0 | ||||
| 10. Round | 08/05/1999 | FC Basel 1893 | - | Grasshopper Club Zürich | 2:0 | |
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| 13. Round | 30/05/1999 | FC Luzern | - | Grasshopper Club Zürich | 1:4 |
Romania