[10] FC Chiasso 0-2 Winterthur [8] 2019-09-24 17:00
Stadium: Stadio comunale Chiasso Round: 8
Referee: Mirel Turkes Home Manager: Stefano Maccoppi Away Manager: Ralf Loose
Head to Head
| Switzerland Challenge League | 2019/05/16 18:00 | Winterthur v FC Chiasso | L | 2-0 |
| Switzerland Challenge League | 2019/02/23 17:30 | FC Chiasso v Winterthur | D | 1-1 |
| Switzerland Challenge League | 2018/12/16 13:30 | FC Chiasso v Winterthur | L | 1-3 |
| Switzerland Challenge League | 2018/09/29 16:00 | Winterthur v FC Chiasso | W | 0-1 |
| Switzerland Challenge League | 2018/05/09 18:00 | Winterthur v FC Chiasso | L | 2-1 |
| Switzerland Challenge League | 2018/03/09 19:00 | FC Chiasso v Winterthur | W | 1-0 |
| Switzerland Challenge League | 2017/11/25 18:00 | FC Chiasso v Winterthur | D | 1-1 |
| Switzerland Challenge League | 2017/09/09 17:00 | Winterthur v FC Chiasso | D | 1-1 |
Home History
| Switzerland Challenge League | 2019/09/21 15:00 | Stade Lausanne-Ouchy v FC Chiasso | L | 3-0 |
| Switzerland Challenge League | 2019/08/31 17:00 | FC Schaffhausen v FC Chiasso | L | 1-0 |
| Switzerland Challenge League | 2019/08/25 14:00 | FC Chiasso v FC Vaduz | D | 2-2 |
| Switzerland Cup | 2019/08/17 16:00 | FC Bulle v FC Chiasso | L | 2-1 |
| Switzerland Challenge League | 2019/08/08 18:00 | FC Chiasso v Aarau | W | 4-2 |
| Switzerland Challenge League | 2019/08/03 15:30 | Kriens v FC Chiasso | L | 2-0 |
| Switzerland Challenge League | 2019/07/27 17:00 | Lausanne Sports v FC Chiasso | L | 3-0 |
| Switzerland Challenge League | 2019/07/20 16:30 | FC Chiasso v Wil 1900 | L | 0-1 |
Away History
| Switzerland Challenge League | 2019/09/21 16:00 | Winterthur v Wil 1900 | L | 0-3 |
| Switzerland Cup | 2019/09/13 18:00 | Winterthur v St Gallen | W | 2-0 |
| Switzerland Challenge League | 2019/08/31 15:30 | Kriens v Winterthur | L | 3-2 |
| Switzerland Challenge League | 2019/08/23 18:00 | Grasshoppers v Winterthur | D | 2-2 |
| Switzerland Cup | 2019/08/17 14:00 | YF Juventus v Winterthur | W | 0-3 |
| Switzerland Challenge League | 2019/08/11 14:00 | FC Vaduz v Winterthur | W | 0-1 |
| Switzerland Challenge League | 2019/08/03 16:00 | Winterthur v Lausanne Sports | L | 0-6 |
| Switzerland Challenge League | 2019/07/30 17:00 | Stade Lausanne-Ouchy v Winterthur | W | 1-2 |