| 1. Round | 04/08/2019 | FC Winterthur II | - | SV Höngg | 2:1 |  |
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| 2. Round | 10/08/2019 | FC Wettswil-Bonstetten | - | FC Winterthur II | 2:1 |  |
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| 16. Round | 17/08/2019 | FC Paradiso | - | FC Winterthur II | 0:3 | ||||
| 4. Round | 24/08/2019 | FC Balzers | - | FC Winterthur II | 1:5 | |
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| 5. Round | 01/09/2019 | FC Winterthur II | - | FC Tuggen | 0:2 | |
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| 6. Round | 07/09/2019 | FC Red Star Zürich | - | FC Winterthur II | 2:0 | ||||
| 7. Round | 14/09/2019 | FC Winterthur II | - | FC Dietikon | 2:2 | |
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| 9. Round | 28/09/2019 | FC Winterthur II | - | FC Thalwil | 3:1 | ||||
| 10. Round | 12/10/2019 | FC Winterthur II | - | FC Gossau | 3:0 | |
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| 11. Round | 19/10/2019 | USV Eschen/Mauren | - | FC Winterthur II | 1:1 | |
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| 12. Round | 27/10/2019 | FC Winterthur II | - | FC Linth 04 | 3:2 | |
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| 14. Round | 09/11/2019 | SV Höngg | - | FC Winterthur II | 1:0 |
Germany