FC Winterthur were Swiss Cup finalists in 1968. Source.
1925-26 32F Grasshoppers 4 - 2 Winterthur
1926-27 32F Winterthur 4 - 0 Birsfelden
16F Töss 2 - 0 Winterthur
1927-28 32F Winterthur 6 - 0 Baden
16F Winterthur 1 - 3 Zürich
1928-29 PR Winterthur 2 - 0 Töss
32F St. Gallen 0 - 4 Winterthur
16F Chiasso 2 - 4 Winterthur
8F Winterthur 5 - 3 Zürich
QF Urania Genève 3 - 0 Winterthur
1929-30 PR Winterthur 7 - 1 Fortuna St. Gallen
32F Winterthur 2 - 1 Birsfelden
16F Winterthur 1 - 2 Blue Stars Zürich
1930-31 32F Old Boys Basel 1 - 2 Winterthur
16F Winterthur 1 - 0 Locarno
8F Winterthur 1 - 3 Nordstern
1931-32 32F Winterthur 3 - 1 Baden
16F Winterthur 2 - 3 Young Fellows Zürich
1932-33 32F Winterthur 2 - 0 Buchs
16F Balerna 0 - 5 Winterthur
8F Zürich 5 - 1 Winterthur
1933-34 32F Winterthur 3 - 2 Black Stars Basel
16F Kickers Lucerne 1 - 4 Winterthur
8F Locarno 2 - 0 Winterthur
1934-35 PR3 Veltheim 0 - 3 Winterthur
32F Töss 0 - 1 Winterthur
16F Winterthur 1 - 4 Chiasso
1935-36 32F Winterthur 2 - 0 Altstetten
16F Winterthur 3 - 1 Arbon
8F Locarno 1 - 0 Winterthur
1936-37 32F Oerlikon/Polizei 2 - 3 Winterthur
16F Schaffhausen 2 - 1 Winterthur
1937-38 32F St. Gallen 3 - 2 Winterthur
1938-39 PR2 Winterthur 9 - 0 Horgen
PR3 Winterthur 2 - 0 Höngg
16F Winterthur 0 - 3 Luzern
1939-40 PR Winterthur 5 - 1 Phoenix Winterthur
R1 Winterthur 4 - 3 Töss
R2 Winterthur 0 - 3 Schaffhausen
1940-41 R1 Winterthur 2 - 1 Tössfeld
R2 Winterthur 4 - 4 Brühl
Brühl 2 - 0 Winterthur
1941-42 R1 Winterthur 0 - 1 Gossau
1942-43 PR Töss 1 - 3 Winterthur
R1 Gossau 1 - 2 Winterthur
R2 Winterthur 1 - 5 Brühl
1943-44 PR1 Winterthur 5 - 2 Tössfeld
PR2 Amriswil 0 - 6 Winterthur
PR3 Winterthur 3 - 2 Frauenfeld
16F Luzern 1 - 0 Winterthur
1944-45 R1 Tössfeld 0 - 2 Winterthur
R2 Winterthur 2 - 1 Phoenix Winterthur
32F Winterthur 1 - 3 Bellinzona
1945-46 PR2 Winterthur 2 - 1 Tössfeld
PR3 Bülach 2 - 3 Winterthur
32F Winterthur 3 - 5 St. Gallen
1946-47 PR2 Wil 0 - 1 Winterthur
32F Red Star 2 - 1 Winterthur
1947-48 PR2 Winterthur 3 - 0 Adliswil
32F Zug 2 - 0 Winterthur
1948-49 PR2 Bischofszell 2 - 3 Winterthur
32F Winterthur 1 - 2 Basel
1949-50 PR2 Winterthur 6 - 0 Ceresio
32F Luxern 4 - 0 Winterthur
1950-51 32F Uster 0 - 2 Winterthur
16F Winterthur 1 - 2 Locarno
1951-52 32F Winterthur 4 - 0 Ceresio
16F Wil 0 - 4 Winterthur
8F Winterthur 0 - 1 International Geneva
1952-53 32F Winterthur 5 - 1 Wetzikon
16F Young Fellows Zürich 3 - 3 Winterthur
Winterthur 2 - 1 Young Fellows Zürich
8F Lausanne 5 - 1 Winterthur
1953-54 16F St. Gallen 0 - 0 Winterthur (abandoned)
St. Gallen 3 - 2 Winterthur
1954-55 32F Winterthur 6 - 2 Küsnacht
16F St. Gallen 3 - 1 Winterthur
1955-56 32F Wil 0 - 2 Winterthur
16F Winterthur 5 - 4 Oerlikon/Polizei
8F Grenchen 1 - 0 Winterthur
1956-57 32F Winterthur 4 - 2 Oerlikon
16F Bodio 0 - 1 Winterthur
8F Luzern 2 - 0 Winterthur
1957-58 32F Winterthur 5 - 1 Baden
16F Brunnen 1 - 1 Winterthur
Winterthur 0 - 1 Brunnen
1958-59 32F Winterthur 5 - 0 Dübendorf
16F Winterthur 4 - 0 Brühl
8F Winterthur 2 - 2 Chiasso
Chiasso 3 - 0 Winterthur
1959-60 32F Winterthur 5 - 0 Vaduz
16F Winterthur 8 - 1 Bodio
8F Urania Genève 1 - 0 Winterthur
1960-61 32F Winterthur 5 - 0 Wil
16F Brühl 0 - 3 Winterthur
8F Chiasso 1 - 0 Winterthur
1961-62 32F Trimbach 1 - 4 Winterthur
16F Winterthur 3 - 1 Locarno
8F Montreux-Sports 2 - 7 Winterthur
QF Young Boys 6 - 1 Winterthur
1962-63 32F Bülach 0 - 2 Winterthur
16F Chiasso 4 - 1 Winterthur
1963-64 32F Winterthur 3 - 0 Krüsnacht
16F Zürich 4 - 0 Winterthur
1964-65 32F Winterthur 0 - 2 Wettingen
1965-66 32F Winterthur 5 - 1 Oerlikon/Polizei
16F Winterthur 0 - 2 Bellinzona
1966-67 16F Winterthur 3 - 0 Frauenfeld
8F Winterthur 3 - 1 Young Boys
QF Winterthur 0 - 3 Lausanne
1967-68 32F Winterthur 10 - 1 Vaduz
16F Winterthur 3 - 0 Amriswil
8F Neuchâtel Xamax 4 - 5 Winterthur
QF Winterthur 2 - 1 Young Fellows Zürich
SF Winterthur 2 - 1 Bienne
F Lugano 2 - 1 Winterthur
1968-69 16F Grenchen 0 - 0 Winterthur
Winterthur 1 - 2 Grenchen
1969-70 16F Luzern 3 - 3 Winterthur
Winterthur 4 - 2 Luzern
8F Winterthur 1 - 1 Servette
Servette 4 - 1 Winterthur
1970-71 16F Winterthur 2 - 0 Burgdorf
8F Winterthur 0 - 0 Zürich
Zürich 3 - 1 Winterthur
1971-72 16F Winterthur 1 - 2 Brühl
1972-73 16F Aarau 2 - 3 Winterthur
8F Uzwil 0 - 2 Winterthur
QF Sion 1 - 2 Winterthur (1st leg)
Winterthur 2 - 1 Sion (2nd leg)
SF Winterthur 1 - 1 Zürich (1st leg)
Zürich 2 - 1 Winterthur (2nd leg)
1973-74 16F Tössfeld 2 - 3 Winterthur
8F Chênois 2 - 1 Winterthur
1974-75 16F Nordstern 2 - 5 Winterthur
8F Kriens 1 - 2 Winterthur
QF Grenchen 2 - 0 Winterthur (1st leg)
Winterthur 2 - 0 Grenchen (2nd leg) (Winterthur won on PK.)
SF Winterthur 2 - 1 Young Boys (1st leg)
Young Boys 0 - 0 Winterthur (2nd leg)
F Basel 2 - 1 Winterthur
1975-76 16F Concordia Basel 0 - 1 Winterthur
8F Winterthur 1 - 4 Sion
1976-77 16F Altstätten 1 - 6 Winterthur
8F Winterthur 0 - 1 St. Gallen
1977-78 PR2 Brugg 3 - 1 Winterthur
1978-79 PR2 Blue Stars 0 - 5 Winterthur
32F Rüti 1 - 3 Winterthur
16F Chur 0 - 4 Winterthur
8F Chênois 4 - 1 Winterthur
1979-80 PR2 Red Star Zürich 0 - 5 Winterthur
32F Bellinzona 1 - 3 Winterthur
16F Winterthur 1 - 0 Lugano
8F Winterthur 2 - 1 La-Chaux-de-Fonds
QF Neuchâtel Xamax 1 - 0 Winterthur
1980-81 PR2 Brühl 2 - 5 Winterthur
32F Frauenfeld 1 - 0 Winterthur
1981-82 PR2 Rüti 1 - 2 Winterthur
32F Balerna 0 - 4 Winterthur
16F Winterthur 4 - 3 Chiasso
8F Sion 3 - 1 Winterthur
1982-83 32F Einsielden 3 - 4 Winterthur
16F Chiasso 1 - 2 Winterthur
8F Chênois 1 - 5 Winterthur
QF Zürich 3 - 1 Winterthur
1983-84 PR2 Schaffhausen 1 - 4 Winterthur
32F Winterthur 3 - 1 Lugano
16F St. Gallen 2 - 0 Winterthur
1984-85 32F Brüttisellen 0 - 5 Winterthur
16F Volketswil 1 - 9 Winterthur
8F Vevey 3 - 1 Winterthur
1985-86 PR2 Bern 0 - 2 Winterthur
32F Rapid Ostermundigen 0 - 6 Winterthur
16F Winterthur 7 - 2 Lugano
8F St. Gallen 0 - 0 Winterthur (St. Gallen won on PK.)
1986-87 PR2 Ponte Tresa 0 - 2 Winterthur
32F Winterthur 2 - 2 Schaffhausen (Winterthur won on PK.)
16F Winterthur 5 - 0 Muri
8F Winterthur 2 - 2 Locarno (Locarno won on PK.)
1987-88 PR2 Brüttisellen 3 - 5 Winterthur
32F Tuggen 0 - 0 Winterthur (Winterthur won on PK.)
16F Old Boys Basel 3 - 1 Winterthur
1988-89 PR2 Kilchberg 0 - 4 Winterthur
32F Altstätten 1 - 4 Winterthur
16F Mendrisio 0 - 2 Winterthur
8F Sion 2 - 1 Winterthur
1989-90 PR2 Stäfa 3 - 3 Winterthur (Winterthur won on PK.)
32F Rorschach 2 - 1 Winterthur
1990-91 PR2 Young Fellows Zürich 0 - 0 Winterthur (Winterthur won on PK.)
32F Winterthur 1 - 3 Grasshoppers
1991-92 PR2 Frauenfeld 2 - 2 Winterthur (Frauenfeld won on PK.)
1992-93 PR2 Wädenswil 2 - 4 Winterthur
32F Winterthur 2 - 5 St. Gallen
1993-94 PR2 Seebach 0 - 8 Winterthur
32F Rorschach 1 - 3 Winterthur
16F Winterthur 1 - 2 Luzern
1994-95 PR2 Hinwil 1 - 4 Winterthur
32F Winterthur 1 - 2 Zürich
1995-96 PR2 Flawil 0 - 5 Winterthur
32F Winterthur 0 - 3 Locarno
1996-97 PR2 Uster 0 - 5 Winterthur
32F Seefeld Zürich 0 - 3 Winterthur
16F Bellinzona 2 - 3 Winterthur
8F Fribourg 1 - 0 Winterthur
1997-98 32F Rapperswil-Jona 0 - 3 Winterthur
16F Winterthur 1 - 1 Luzern (Winterthur won on PK.)
8F Winterthur 1 - 3 Lausanne-Sport
1998-99 32F Winterthur 5 - 1 Rapperswil-Jona
16F Winterthur 1 - 2 Grasshoppers
1999-00 32F Dornach 0 - 1 Winterthur
16F Winterthur 1 - 3 Aarau
2000-01 32F St. Gallen II 1 - 2 Winterthur
16F Winterthur 1 - 0 Lugano
8F Schaffhausen 2 - 3 Winterthur
QF Winterthur 1 - 3 St. Gallen
2001-02 32F Schötz 2 - 1 Winterthur
2002-03 32F Zürich U-21 2 - 2 Winterthur (Zürich U-21 won on PK.)
2003-04 32F Dietikon 1 - 3 Winterthur
16F Kriens 1 - 2 Winterthur
8F Winterthur 2 - 3 Neuchâtel Xamax
2004-05 32F Affoltern 1 - 5 Winterthur
16F Winterthur 1 - 3 Luzern
2005-06 32F Cham 0 - 1 Winterthur
16F Winterthur 4 - 2 Grasshoppers
8F Winterthur 2 - 0 Lucerne
QF Servette 1 - 3 Winterthur
SF Winterthur 0 - 1 Sion
2006-07 32F Flums 0 - 12 Winterthur
16F Wohlen 1 - 3 Winterthur
8F Winterthur 1 - 2 Aarau
2007-08 32F Red Star Zürich 0 - 5 Winterthur
16F Winterthur 2 - 3 Grasshoppers
2008-09 32F Seefeld Zürich 0 - 0 Winterthur (Seefeld won on PK.)
2009-10 32F Frauenfeld 0 - 8 Winterthur
16F Tuggen 1 - 3 Winterthur
8F Winterthur 2 - 4 Thun
2010-11 R1 Freienbach 2 - 3 Winterthur
R2 Wohlen 5 - 1 Winterthur
2011-12 32F Baden 0 - 1 Winterthur
16F Winterthur 2 - 0 Brühl
8F Winterthur 1 - 1 Young Boys (Winterthur won on PK.)
QF Winterthur 2 - 2 St. Gallen (Winterthur won on PK.)
SF Winterthur 1 - 2 Basel
2012-13 32F Eschenbach 0 - 1 Winterthur
16F Köniz 2 - 2 Winterthur (Köniz won on PK.)
2013-14 32F Brühl 0 - 0 Winterthur (Brühl won on PK.)
2014-15 32F Eschenbach 1 - 3 Winterthur
16F Winterthur 0 - 4 Basel
2015-16 32F Delémont 0 - 1 Winterthur
16F Winterthur 1 - 1 Biel-Bienne (Winterthur won on PK.)
8F Winterthur 0 - 2 Lugano
2016-17 32F Yverdon Sport 1 - 4 Winterthur
16F Stade-Lausanne-Ouchy 0 - 3 Winterthur
8F Winterthur 2 - 1 Chiasso
QF Young Boys 2 - 2 Winterthur (Winterthur won on PK.)
SF Winterthur 1 - 3 Basel
2017-18 R1 Gambarogno-Contone 1 - 6 Winterthur
R2 Delémont 4 - 2 Winterthur
2018-19 R1 Greifensee 0 - 3 Winterthur
R2 Bellinzona 1 - 2 Winterthur
R3 Winterthur 0 - 1 Basel
(Source: Italian, German Wikipedia; RSSSF.) I'm not convinced I've seen every qualifying round score.
Which clubs have knocked Winterthur out of the cup the most often?
9 St. Gallen
7 Zürich (+1 Zürich U-21)
6 Luzern
6 Basel
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