| 2. Round | 26/08/2023 | FC Luzern [Youth B] | - | FC Winterthur [Youth B] | 1:0 | ||||
| 4. Round | 09/09/2023 | FCO St. Gallen [Youth B] | - | FC Winterthur [Youth B] | 3:0 dec. | ||||
| 8. Round | 14/10/2023 | FC Thun Berner Oberland [Youth B] | - | FC Winterthur [Youth B] | 2:1 | ||||
| 11. Round | 05/11/2023 | FC Winterthur [Youth B] | - | FC Sion [Youth B] | 3:2 | ||||
| 18. Round | 24/02/2024 | Servette FC [Youth B] | - | FC Winterthur [Youth B] | 4:3 | ||||
| 21. Round | 23/03/2024 | FC Lausanne-Sport [Youth B] | - | FC Winterthur [Youth B] | 1:0 | ||||
| 22. Round | 06/04/2024 | FC Winterthur [Youth B] | - | BSC Young Boys [Youth B] | 3:1 | ||||
| 23. Round | 13/04/2024 | FC Sion [Youth B] | - | FC Winterthur [Youth B] | 3:0 | ||||
| 24. Round | 20/04/2024 | FC Winterthur [Youth B] | - | FC Aarau [Youth B] | 8:0 |  |
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| 26. Round | 04/05/2024 | Grasshopper Club Zürich [Youth B] | - | FC Winterthur [Youth B] | 0:4 |
Eritrea