| 1. Round | 21/08/2019 | FCO St. Gallen/Wil [U18] | - | FC Winterthur [U18] | 3:3 | ||||
| 2. Round | 24/08/2019 | Team Xamax-BEJUNE FA [U18] | - | FC Winterthur [U18] | 2:0 | ||||
| 3. Round | 31/08/2019 | FC Winterthur [U18] | - | BSC Young Boys [U18] | 1:6 | ||||
| 4. Round | 07/09/2019 | FC Sion [U18] | - | FC Winterthur [U18] | 5:1 | ||||
| 6. Round | 21/09/2019 | FC Zürich [U18] | - | FC Winterthur [U18] | 1:0 | ||||
| 7. Round | 28/09/2019 | FC Winterthur [U18] | - | Team Aargau [U18] | 3:4 | ||||
| 8. Round | 12/10/2019 | Team FC Luzern/SC Kriens [U18] | - | FC Winterthur [U18] | 2:3 |  |
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| 9. Round | 26/10/2019 | Grasshopper Club Zürich [U18] | - | FC Winterthur [U18] | 1:4 | ||||
| 10. Round | 02/11/2019 | FC Winterthur [U18] | - | Team Vaud Lausanne [U18] | 1:2 | |
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| 11. Round | 16/11/2019 | Team Ticino [U18] | - | FC Winterthur [U18] | 0:1 | ||||
| 13. Round | 30/11/2019 | FC Winterthur [U18] | - | FC Basel 1893 [U18] | 0:2 |
Switzerland