| 1. Round | 06/08/2023 | FC Winterthur II | - | FC Linth 04 | 1:1 | ||||
| 2. Round | 12/08/2023 | FC Kosova Zürich | - | FC Winterthur II | 0:0 | ||||
| 3. Round | 20/08/2023 | FC Winterthur II | - | Grasshopper Club Zürich II | 3:0 |  |
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| 5. Round | 03/09/2023 | FC Winterthur II | - | SV Höngg | 2:0 |  |
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| 6. Round | 09/09/2023 | FC Uzwil | - | FC Winterthur II | 0:2 | ||||
| 4. Round | 13/09/2023 | FC Freienbach | - | FC Winterthur II | 2:1 | ||||
| 7. Round | 16/09/2023 | FC Winterthur II | - | USV Eschen/Mauren | 1:2 | ||||
| 8. Round | 23/09/2023 | FC Tuggen | - | FC Winterthur II | 0:2 | ||||
| 9. Round | 01/10/2023 | FC Winterthur II | - | SC YF/Juventus Zürich | 3:1 | ||||
| 10. Round | 08/10/2023 | FC Mendrisio | - | FC Winterthur II | 0:0 | ||||
| 11. Round | 14/10/2023 | FC Winterthur II | - | AC Taverne | 1:2 | ||||
| 12. Round | 28/10/2023 | FC Kreuzlingen | - | FC Winterthur II | 3:3 | ||||
| 13. Round | 05/11/2023 | FC Winterthur II | - | FC Gossau | 3:0 | |
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| 15. Round | 18/11/2023 | FC Winterthur II | - | FC Wettswil-Bonstetten | 1:2 | ||||
| 19. Round | 10/03/2024 | FC Winterthur II | - | FC Freienbach | 5:0 | |
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| 21. Round | 23/03/2024 | FC Winterthur II | - | FC Uzwil | 4:1 | ||||
| 23. Round | 07/04/2024 | FC Winterthur II | - | FC Tuggen | 0:2 |
Switzerland