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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1936 | Road Cycling | Milan–San Remo | Monument | Men | Angelo Varetto | Italy | 1 |
| 1935 | Road Cycling | Milan–San Remo | Monument | Men | Giuseppe Olmo | Italy | 1 |
| 1934 | Road Cycling | Milan–San Remo | Monument | Men | Jef Demuysere | Belgium | 1 |
| 1933 | Road Cycling | Milan–San Remo | Monument | Men | Learco Guerra | Italy | 1 |
| 1932 | Road Cycling | Milan–San Remo | Monument | Men | Alfredo Bovet | Italy | 1 |
| 1931 | Road Cycling | Milan–San Remo | Monument | Men | Alfredo Binda | Italy | 1 |
| 1930 | Road Cycling | Milan–San Remo | Monument | Men | Michele Mara | Italy | 1 |
| 1929 | Road Cycling | Milan–San Remo | Monument | Men | Alfredo Binda | Italy | 1 |
| 1928 | Road Cycling | Milan–San Remo | Monument | Men | Costante Girardengo | Italy | 1 |
| 1927 | Road Cycling | Milan–San Remo | Monument | Men | Pietro Chesi | Italy | 1 |
| 1926 | Road Cycling | Milan–San Remo | Monument | Men | Costante Girardengo | Italy | 1 |
| 1925 | Road Cycling | Milan–San Remo | Monument | Men | Costante Girardengo | Italy | 1 |
| 1924 | Road Cycling | Milan–San Remo | Monument | Men | Pietro Linari | Italy | 1 |
| 1923 | Road Cycling | Milan–San Remo | Monument | Men | Costante Girardengo | Italy | 1 |
| 1922 | Road Cycling | Milan–San Remo | Monument | Men | Giovanni Brunero | Italy | 1 |
| 1921 | Road Cycling | Milan–San Remo | Monument | Men | Costante Girardengo | Italy | 1 |
| 1920 | Road Cycling | Milan–San Remo | Monument | Men | Gaetano Belloni | Italy | 1 |
| 1919 | Road Cycling | Milan–San Remo | Monument | Men | Angelo Gremo | Italy | 1 |
| 1918 | Road Cycling | Milan–San Remo | Monument | Men | Costante Girardengo | Italy | 1 |
| 1917 | Road Cycling | Milan–San Remo | Monument | Men | Gaetano Belloni | Italy | 1 |
| 1915 | Road Cycling | Milan–San Remo | Monument | Men | Ezio Corlaita | Italy | 1 |
| 1914 | Road Cycling | Milan–San Remo | Monument | Men | Ugo Agostoni | Italy | 1 |
| 1913 | Road Cycling | Milan–San Remo | Monument | Men | Odile Defraye | Belgium | 1 |
| 1912 | Road Cycling | Milan–San Remo | Monument | Men | Henri Pélissier | France | 1 |
| 1911 | Road Cycling | Milan–San Remo | Monument | Men | Gustave Garrigou | France | 1 |
| 1910 | Road Cycling | Milan–San Remo | Monument | Men | Eugene Christophe | France | 1 |
| 1909 | Road Cycling | Milan–San Remo | Monument | Men | Luigi Ganna | Italy | 1 |
| 1908 | Road Cycling | Milan–San Remo | Monument | Men | Cyrille van Hauwaert | Belgium | 1 |
| 1907 | Road Cycling | Milan–San Remo | Monument | Men | Lucien Petit-Breton | France | 1 |
| 2025 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Tadej Pogačar | Slovenia | 1 |
| 2024 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Tadej Pogačar | Slovenia | 1 |
| 2023 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Remco Evenepoel | Belgium | 1 |
| 2022 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Remco Evenepoel | Belgium | 1 |
| 2021 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Tadej Pogačar | Slovenia | 1 |
| 2020 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Primož Roglič | Slovenia | 1 |
| 2019 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Jakob Fuglsang | Denmark | 1 |
| 2018 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Bob Jungels | Luxembourg | 1 |
| 2017 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Alejandro Valverde | Spain | 1 |
| 2016 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Wout Poels | Netherlands | 1 |
| 2015 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Alejandro Valverde | Spain | 1 |
| 2014 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Simon Gerrans | Australia | 1 |
| 2013 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Dan Martin | Ireland | 1 |
| 2012 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Maxim Iglinsky | Kazakhstan | 1 |
| 2011 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Philippe Gilbert | Belgium | 1 |
| 2010 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Alexander Vinokourov | Kazakhstan | 1 |
| 2009 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Andy Schleck | Luxembourg | 1 |
| 2008 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Alejandro Valverde | Spain | 1 |
| 2007 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Danilo Di Luca | Italy | 1 |
| 2006 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Alejandro Valverde | Spain | 1 |
| 2005 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Alexander Vinokourov | Kazakhstan | 1 |
| 2004 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Davide Rebellin | Italy | 1 |
| 2003 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Tyler Hamilton | United States | 1 |
| 2002 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Paolo Bettini | Italy | 1 |
| 2001 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Oscar Camenzind | Switzerland | 1 |
| 2000 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Paolo Bettini | Italy | 1 |
| 1999 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Frank Vandenbroucke | Belgium | 1 |
| 1998 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Michele Bartoli | Italy | 1 |
| 1997 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Michele Bartoli | Italy | 1 |
| 1996 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Pascal Richard | Switzerland | 1 |
| 1995 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Mauro Gianetti | Switzerland | 1 |
| 1994 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Evgeni Berzin | Russia | 1 |
| 1993 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Rolf Sørensen | Denmark | 1 |
| 1992 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Dirk de Wolf | Belgium | 1 |
| 1991 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Moreno Argentin | Italy | 1 |
| 1990 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Eric van Lancker | Belgium | 1 |
| 1989 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Sean Kelly | Ireland | 1 |
| 1988 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Adri van der Poel | Netherlands | 1 |
| 1987 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Moreno Argentin | Italy | 1 |
| 1986 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Moreno Argentin | Italy | 1 |
| 1985 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Moreno Argentin | Italy | 1 |
| 1984 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Sean Kelly | Ireland | 1 |
| 1983 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Steven Rooks | Netherlands | 1 |
| 1982 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Silvano Contini | Italy | 1 |
| 1981 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Josef Fuchs | Switzerland | 1 |
| 1980 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Bernard Hinault | France | 1 |
| 1979 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Dietrich Thurau | West Germany | 1 |
| 1978 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Joseph Bruyère | Belgium | 1 |
| 1977 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Bernard Hinault | France | 1 |
| 1976 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Joseph Bruyère | Belgium | 1 |
| 1975 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1974 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Georges Pintens | Belgium | 1 |
| 1973 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1972 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1971 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1970 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Roger De Vlaeminck | Belgium | 1 |
| 1969 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1968 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Walter Van Sweefelt | Belgium | 1 |
| 1967 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Walter Godefroot | Belgium | 1 |
| 1966 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Jacques Anquetil | France | 1 |
| 1965 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Carmine Preziosi | Italy | 1 |
| 1964 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Willy Blocklandt | Belgium | 1 |
| 1963 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Frans Melckenbeeck | Belgium | 1 |
| 1962 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Jef Planckaert | Belgium | 1 |
| 1961 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Rik Van Looy | Belgium | 1 |
| 1960 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Albertus Geldermans | Netherlands | 1 |
| 1959 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Fred De Bruyne | Belgium | 1 |
| 1958 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Fred De Bruyne | Belgium | 1 |
| 1957 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Germain Derycke | Belgium | 1 |
| 1957 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Frans Schoubben | Belgium | 1 |
| 1956 | Road Cycling | Liège–Bastogne–Liège | Monument | Men | Fred De Bruyne | Belgium | 1 |
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