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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1931 | Road Cycling | World championship | Classics | Men | Learco Guerra | Italy | 1 |
| 1930 | Road Cycling | World championship | Classics | Men | Georges Ronsse | Belgium | 3 |
| 1930 | Road Cycling | World championship | Classics | Men | Learco Guerra | Italy | 2 |
| 1930 | Road Cycling | World championship | Classics | Men | Alfredo Binda | Italy | 1 |
| 1929 | Road Cycling | World championship | Classics | Men | Alfredo Binda | Italy | 3 |
| 1929 | Road Cycling | World championship | Classics | Men | Nicolas Frantz | Luxembourg | 2 |
| 1929 | Road Cycling | World championship | Classics | Men | Georges Ronsse | Belgium | 1 |
| 1928 | Road Cycling | World championship | Classics | Men | Bruno Wolke | Germany | 3 |
| 1928 | Road Cycling | World championship | Classics | Men | Herbert Nebe | Germany | 2 |
| 1928 | Road Cycling | World championship | Classics | Men | Georges Ronsse | Belgium | 1 |
| 1927 | Road Cycling | World championship | Classics | Men | Domenico Piemontesi | Italy | 3 |
| 1927 | Road Cycling | World championship | Classics | Men | Costante Girardengo | Italy | 2 |
| 1927 | Road Cycling | World championship | Classics | Men | Alfredo Binda | Italy | 1 |
| 2025 | Road Cycling | Milan–San Remo | Monument | Men | Mathieu van der Poel | Netherlands | 1 |
| 2024 | Road Cycling | Milan–San Remo | Monument | Men | Jasper Philipsen | Belgium | 1 |
| 2023 | Road Cycling | Milan–San Remo | Monument | Men | Mathieu van der Poel | Netherlands | 1 |
| 2022 | Road Cycling | Milan–San Remo | Monument | Men | Matej Mohorič | Slovenia | 1 |
| 2021 | Road Cycling | Milan–San Remo | Monument | Men | Jasper Stuyven | Belgium | 1 |
| 2020 | Road Cycling | Milan–San Remo | Monument | Men | Wout van Aert | Belgium | 1 |
| 2019 | Road Cycling | Milan–San Remo | Monument | Men | Julian Alaphilippe | France | 1 |
| 2018 | Road Cycling | Milan–San Remo | Monument | Men | Vincenzo Nibali | Italy | 1 |
| 2017 | Road Cycling | Milan–San Remo | Monument | Men | Michał Kwiatkowski | Poland | 1 |
| 2016 | Road Cycling | Milan–San Remo | Monument | Men | Arnaud Démare | France | 1 |
| 2015 | Road Cycling | Milan–San Remo | Monument | Men | John Degenkolb | Germany | 1 |
| 2014 | Road Cycling | Milan–San Remo | Monument | Men | Alexander Kristoff | Norway | 1 |
| 2013 | Road Cycling | Milan–San Remo | Monument | Men | Gerald Ciolek | Germany | 1 |
| 2012 | Road Cycling | Milan–San Remo | Monument | Men | Simon Gerrans | Australia | 1 |
| 2011 | Road Cycling | Milan–San Remo | Monument | Men | Matthew Goss | Australia | 1 |
| 2010 | Road Cycling | Milan–San Remo | Monument | Men | Óscar Freire | Spain | 1 |
| 2009 | Road Cycling | Milan–San Remo | Monument | Men | Mark Cavendish | Great Britain | 1 |
| 2008 | Road Cycling | Milan–San Remo | Monument | Men | Fabian Cancellara | Switzerland | 1 |
| 2007 | Road Cycling | Milan–San Remo | Monument | Men | Óscar Freire | Spain | 1 |
| 2006 | Road Cycling | Milan–San Remo | Monument | Men | Filippo Pozzato | Italy | 1 |
| 2005 | Road Cycling | Milan–San Remo | Monument | Men | Alessandro Petacchi | Italy | 1 |
| 2004 | Road Cycling | Milan–San Remo | Monument | Men | Óscar Freire | Spain | 1 |
| 2003 | Road Cycling | Milan–San Remo | Monument | Men | Paolo Bettini | Italy | 1 |
| 2002 | Road Cycling | Milan–San Remo | Monument | Men | Mario Cipollini | Italy | 1 |
| 2001 | Road Cycling | Milan–San Remo | Monument | Men | Erik Zabel | Germany | 1 |
| 2000 | Road Cycling | Milan–San Remo | Monument | Men | Erik Zabel | Germany | 1 |
| 1999 | Road Cycling | Milan–San Remo | Monument | Men | Andrei Tchmil | Moldova | 1 |
| 1998 | Road Cycling | Milan–San Remo | Monument | Men | Erik Zabel | Germany | 1 |
| 1997 | Road Cycling | Milan–San Remo | Monument | Men | Erik Zabel | Germany | 1 |
| 1996 | Road Cycling | Milan–San Remo | Monument | Men | Gabriele Colombo | Italy | 1 |
| 1995 | Road Cycling | Milan–San Remo | Monument | Men | Laurent Jalabert | France | 1 |
| 1994 | Road Cycling | Milan–San Remo | Monument | Men | Giorgio Furlan | Italy | 1 |
| 1993 | Road Cycling | Milan–San Remo | Monument | Men | Maurizio Fondriest | Italy | 1 |
| 1992 | Road Cycling | Milan–San Remo | Monument | Men | Sean Kelly | Ireland | 1 |
| 1991 | Road Cycling | Milan–San Remo | Monument | Men | Claudio Chiappucci | Italy | 1 |
| 1990 | Road Cycling | Milan–San Remo | Monument | Men | Gianni Bugno | Italy | 1 |
| 1989 | Road Cycling | Milan–San Remo | Monument | Men | Laurent Fignon | France | 1 |
| 1988 | Road Cycling | Milan–San Remo | Monument | Men | Laurent Fignon | France | 1 |
| 1987 | Road Cycling | Milan–San Remo | Monument | Men | Erich Mächler | Switzerland | 1 |
| 1986 | Road Cycling | Milan–San Remo | Monument | Men | Sean Kelly | Ireland | 1 |
| 1985 | Road Cycling | Milan–San Remo | Monument | Men | Hennie Kuiper | Netherlands | 1 |
| 1984 | Road Cycling | Milan–San Remo | Monument | Men | Francesco Moser | Italy | 1 |
| 1983 | Road Cycling | Milan–San Remo | Monument | Men | Giuseppe Saronni | Italy | 1 |
| 1982 | Road Cycling | Milan–San Remo | Monument | Men | Marc Gomez | France | 1 |
| 1981 | Road Cycling | Milan–San Remo | Monument | Men | Fons De Wolf | Belgium | 1 |
| 1980 | Road Cycling | Milan–San Remo | Monument | Men | Pierino Gavazzi | Italy | 1 |
| 1979 | Road Cycling | Milan–San Remo | Monument | Men | Roger De Vlaeminck | Belgium | 1 |
| 1978 | Road Cycling | Milan–San Remo | Monument | Men | Roger De Vlaeminck | Belgium | 1 |
| 1977 | Road Cycling | Milan–San Remo | Monument | Men | Jan Raas | Netherlands | 1 |
| 1976 | Road Cycling | Milan–San Remo | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1975 | Road Cycling | Milan–San Remo | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1974 | Road Cycling | Milan–San Remo | Monument | Men | Felice Gimondi | Italy | 1 |
| 1973 | Road Cycling | Milan–San Remo | Monument | Men | Roger De Vlaeminck | Belgium | 1 |
| 1972 | Road Cycling | Milan–San Remo | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1971 | Road Cycling | Milan–San Remo | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1970 | Road Cycling | Milan–San Remo | Monument | Men | Michele Dancelli | Italy | 1 |
| 1969 | Road Cycling | Milan–San Remo | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1968 | Road Cycling | Milan–San Remo | Monument | Men | Rudi Altig | West Germany | 1 |
| 1967 | Road Cycling | Milan–San Remo | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1966 | Road Cycling | Milan??San Remo | Monument | Men | Eddy Merckx | Belgium | 1 |
| 1965 | Road Cycling | Milan–San Remo | Monument | Men | Arie den Hartog | Netherlands | 1 |
| 1964 | Road Cycling | Milan–San Remo | Monument | Men | Tom Simpson | Great Britain | 1 |
| 1963 | Road Cycling | Milan–San Remo | Monument | Men | Joseph Groussard | France | 1 |
| 1962 | Road Cycling | Milan–San Remo | Monument | Men | Emile Daems | Belgium | 1 |
| 1961 | Road Cycling | Milan–San Remo | Monument | Men | Raymond Poulidor | France | 1 |
| 1960 | Road Cycling | Milan–San Remo | Monument | Men | René Privat | France | 1 |
| 1959 | Road Cycling | Milan–San Remo | Monument | Men | Miguel Poblet | Spain | 1 |
| 1958 | Road Cycling | Milan–San Remo | Monument | Men | Rik Van Looy | Belgium | 1 |
| 1957 | Road Cycling | Milan–San Remo | Monument | Men | Miguel Poblet | Spain | 1 |
| 1956 | Road Cycling | Milan–San Remo | Monument | Men | Fred De Bruyne | Belgium | 1 |
| 1955 | Road Cycling | Milan–San Remo | Monument | Men | Germain Derycke | Belgium | 1 |
| 1954 | Road Cycling | Milan–San Remo | Monument | Men | Rik Van Steenbergen | Belgium | 1 |
| 1953 | Road Cycling | Milan–San Remo | Monument | Men | Loretto Petrucci | Italy | 1 |
| 1952 | Road Cycling | Milan–San Remo | Monument | Men | Loretto Petrucci | Italy | 1 |
| 1951 | Road Cycling | Milan–San Remo | Monument | Men | Louison Bobet | France | 1 |
| 1950 | Road Cycling | Milan–San Remo | Monument | Men | Gino Bartali | Italy | 1 |
| 1949 | Road Cycling | Milan–San Remo | Monument | Men | Fausto Coppi | Italy | 1 |
| 1948 | Road Cycling | Milan–San Remo | Monument | Men | Fausto Coppi | Italy | 1 |
| 1947 | Road Cycling | Milan–San Remo | Monument | Men | Gino Bartali | Italy | 1 |
| 1946 | Road Cycling | Milan–San Remo | Monument | Men | Fausto Coppi | Italy | 1 |
| 1943 | Road Cycling | Milan–San Remo | Monument | Men | Cino Cinelli | Italy | 1 |
| 1942 | Road Cycling | Milan–San Remo | Monument | Men | Adolfo Leoni | Italy | 1 |
| 1941 | Road Cycling | Milan–San Remo | Monument | Men | Pierino Favalli | Italy | 1 |
| 1940 | Road Cycling | Milan–San Remo | Monument | Men | Gino Bartali | Italy | 1 |
| 1939 | Road Cycling | Milan–San Remo | Monument | Men | Gino Bartali | Italy | 1 |
| 1938 | Road Cycling | Milan–San Remo | Monument | Men | Giuseppe Olmo | Italy | 1 |
| 1937 | Road Cycling | Milan–San Remo | Monument | Men | Cesare Del Cancia | Italy | 1 |
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