This page lists the head-to-head record of FC Chiasso vs FC Winterthur including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | FC Winterthur | FC Chiasso | Draws |
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| Total Matches | 51 | 25 | 10 | 16 |
| At Schutzenwiese | 25 | 11 | 5 | 9 |
| At Stadio Comunale | 26 | 14 | 5 | 7 |
| Cup Matches | 1 | 1 | 0 | 0 |
| Challenge League Matches | 50 | 24 | 10 | 16 |
| Total Goals Scored | 108 | 67 | 41 | |
Last 50 FC Winterthur vs FC Chiasso Matches
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| 2021 7 May | | Challenge League | Chiasso | 2 - 1 | Winterthur |
| 2021 3 April | | Challenge League | Winterthur | 0 - 1 | Chiasso |
| 2021 23 January | | Challenge League | Chiasso | 0 - 3 | Winterthur |
| 2020 2 December | | Challenge League | Winterthur | 2 - 0 | Chiasso |
| 2020 17 July | | Challenge League | Chiasso | 0 - 2 | Winterthur |
| 2020 2 February | | Challenge League | Winterthur | 3 - 2 | Chiasso |
| 2019 26 October | | Challenge League | Winterthur | 2 - 1 | Chiasso |
| 2019 24 September | | Challenge League | Chiasso | 0 - 2 | Winterthur |
| 2019 16 May | | Challenge League | Winterthur | 2 - 0 | Chiasso |
| 2019 23 February | | Challenge League | Chiasso | 1 - 1 | Winterthur |
| 2018 16 December | | Challenge League | Chiasso | 1 - 3 | Winterthur |
| 2018 29 September | | Challenge League | Winterthur | 0 - 1 | Chiasso |
| 2018 9 May | | Challenge League | Winterthur | 2 - 1 | Chiasso |
| 2018 9 March | | Challenge League | Chiasso | 1 - 0 | Winterthur |
| 2017 25 November | | Challenge League | Chiasso | 1 - 1 | Winterthur |
| 2017 9 September | | Challenge League | Winterthur | 1 - 1 | Chiasso |
| 2017 3 June | | Challenge League | Winterthur | 3 - 1 | Chiasso |
| 2017 4 February | | Challenge League | Chiasso | 4 - 1 | Winterthur |
| 2016 26 October | | Cup | Winterthur | 2 - 1 | Chiasso |
| 2016 15 October | | Challenge League | Winterthur | 1 - 1 | Chiasso |
| 2016 6 August | | Challenge League | Chiasso | 0 - 1 | Winterthur |
| 2016 27 May | | Challenge League | Winterthur | 0 - 0 | Chiasso |
| 2016 19 March | | Challenge League | Chiasso | 1 - 2 | Winterthur |
| 2015 28 November | | Challenge League | Chiasso | 1 - 3 | Winterthur |
| 2015 23 September | | Challenge League | Winterthur | 3 - 1 | Chiasso |
| 2015 17 May | | Challenge League | Chiasso | 0 - 0 | Winterthur |
| 2015 11 April | | Challenge League | Winterthur | 0 - 0 | Chiasso |
| 2014 5 October | | Challenge League | Chiasso | 1 - 1 | Winterthur |
| 2014 2 August | | Challenge League | Winterthur | 1 - 0 | Chiasso |
| 2014 10 May | | Challenge League | Chiasso | 0 - 0 | Winterthur |
| 2014 29 March | | Challenge League | Winterthur | 1 - 1 | Chiasso |
| 2013 7 December | | Challenge League | Chiasso | 1 - 0 | Winterthur |
| 2013 27 July | | Challenge League | Winterthur | 1 - 0 | Chiasso |
| 2013 20 April | | Challenge League | Chiasso | 0 - 1 | Winterthur |
| 2013 17 March | | Challenge League | Winterthur | 3 - 1 | Chiasso |
| 2012 1 October | | Challenge League | Winterthur | 1 - 1 | Chiasso |
| 2012 5 August | | Challenge League | Chiasso | 0 - 1 | Winterthur |
| 2012 5 April | | Challenge League | Chiasso | 1 - 2 | Winterthur |
| 2011 23 October | | Challenge League | Winterthur | 0 - 0 | Chiasso |
| 2011 20 February | | Challenge League | Winterthur | 1 - 2 | Chiasso |
| 2010 11 September | | Challenge League | Chiasso | 1 - 1 | Winterthur |
| 2008 4 April | | Challenge League | Chiasso | 1 - 1 | Winterthur |
| 2007 26 September | | Challenge League | Winterthur | 2 - 0 | Chiasso |
| 2007 8 May | | Challenge League | Winterthur | 3 - 0 | Chiasso |
| 2006 4 November | | Challenge League | Chiasso | 1 - 1 | Winterthur |
| 2006 25 March | | Challenge League | Winterthur | 2 - 1 | Chiasso |
| 2005 19 August | | Challenge League | Chiasso | 1 - 1 | Winterthur |
| 2005 1 April | | Challenge League | Chiasso | 0 - 1 | Winterthur |
| 2004 9 September | | Challenge League | Winterthur | 0 - 1 | Chiasso |
| 2003 24 October | | Challenge League | Chiasso | 2 - 1 | Winterthur |
Biggest FC Winterthur Victory vs FC Chiasso
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| 2021 23 January | | Challenge League | Chiasso | 0 - 3 | Winterthur |
Biggest FC Chiasso Victory vs FC Winterthur
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| 2017 4 February | | Challenge League | Chiasso | 4 - 1 | Winterthur |
Biggest FC Winterthur Defeat vs FC Chiasso
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| 2017 4 February | | Challenge League | Chiasso | 4 - 1 | Winterthur |
Biggest FC Chiasso Defeat vs FC Winterthur
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| 2021 23 January | | Challenge League | Chiasso | 0 - 3 | Winterthur |
Last 5 FC Winterthur Home Matches
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| 2024 9 November | | Super League | Winterthur | 1 - 0 | Lausanne Sport |
| 2024 26 October | | Super League | Winterthur | 1 - 6 | Basel |
| 2024 5 October | | Super League | Winterthur | 1 - 0 | Grasshopper |
| 2024 22 September | | Super League | Winterthur | 1 - 4 | Young Boys |
| 2024 1 September | | Super League | Winterthur | 0 - 1 | Servette |
Last 5 FC Chiasso Home Matches
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| 2021 27 October | | Cup | Chiasso | 1 - 1 | St. Gallen |
| 2021 20 May | | Challenge League | Chiasso | 2 - 1 | Neuchatel Xamax |
| 2021 7 May | | Challenge League | Chiasso | 2 - 1 | Winterthur |
| 2021 23 April | | Challenge League | Chiasso | 2 - 1 | Stade Lausanne-Ouchy |
| 2021 20 April | | Challenge League | Chiasso | 2 - 2 | Grasshopper |
Last 5 FC Winterthur Away Matches
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| 2024 2 November | | Super League | Basel | 5 - 0 | Winterthur |
| 2024 30 October | | Super League | St. Gallen | 2 - 2 | Winterthur |
| 2024 20 October | | Super League | Lausanne Sport | 2 - 0 | Winterthur |
| 2024 29 September | | Super League | Lugano | 2 - 1 | Winterthur |
| 2024 14 September | | Cup | Wil | 1 - 1 | Winterthur |
Last 5 FC Chiasso Away Matches
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| 2022 20 August | | Cup | Rotkreuz | 3 - 0 | Chiasso |
| 2021 19 September | | Cup | Porrentruy | 0 - 3 | Chiasso |
| 2021 14 August | | Cup | Unterstrass | 1 - 1 | Chiasso |
| 2021 14 May | | Challenge League | FC Schaffhausen | 1 - 1 | Chiasso |
| 2021 11 May | | Challenge League | Wil | 3 - 2 | Chiasso |