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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1966 | Road Cycling | La Flèche Wallonne | Classics | Men | Michele Dancelli | Italy | 1 |
| 1965 | Road Cycling | La Flèche Wallonne | Classics | Men | Roberto Poggiali | Italy | 1 |
| 1964 | Road Cycling | La Flèche Wallonne | Classics | Men | Gilbert Desmet | Belgium | 1 |
| 1963 | Road Cycling | La Flèche Wallonne | Classics | Men | Raymond Poulidor | France | 1 |
| 1962 | Road Cycling | La Flèche Wallonne | Classics | Men | Henri De Wolf | Belgium | 1 |
| 1961 | Road Cycling | La Flèche Wallonne | Classics | Men | Willy Vannitsen | Belgium | 1 |
| 1960 | Road Cycling | La Flèche Wallonne | Classics | Men | Pino Cerami | Belgium | 1 |
| 1959 | Road Cycling | La Flèche Wallonne | Classics | Men | Jos Hoevenaers | Belgium | 1 |
| 1958 | Road Cycling | La Flèche Wallonne | Classics | Men | Rik Van Steenbergen | Belgium | 1 |
| 1957 | Road Cycling | La Flèche Wallonne | Classics | Men | Raymond Impanis | Belgium | 1 |
| 1956 | Road Cycling | La Flèche Wallonne | Classics | Men | Richard Van Genechten | Belgium | 1 |
| 1955 | Road Cycling | La Flèche Wallonne | Classics | Men | Stan Ockers | Belgium | 1 |
| 1954 | Road Cycling | La Flèche Wallonne | Classics | Men | Germain Derycke | Belgium | 1 |
| 1953 | Road Cycling | La Flèche Wallonne | Classics | Men | Stan Ockers | Belgium | 1 |
| 1952 | Road Cycling | La Flèche Wallonne | Classics | Men | Ferdi Kübler | Switzerland | 1 |
| 1951 | Road Cycling | La Flèche Wallonne | Classics | Men | Ferdi Kübler | Switzerland | 1 |
| 1950 | Road Cycling | La Flèche Wallonne | Classics | Men | Fausto Coppi | Italy | 1 |
| 1949 | Road Cycling | La Flèche Wallonne | Classics | Men | Rik Van Steenbergen | Belgium | 1 |
| 1948 | Road Cycling | La Flèche Wallonne | Classics | Men | Fermo Camellini | Italy | 1 |
| 1947 | Road Cycling | La Flèche Wallonne | Classics | Men | Ernest Sterckx | Belgium | 1 |
| 1946 | Road Cycling | La Flèche Wallonne | Classics | Men | Désiré Keteleer | Belgium | 1 |
| 1945 | Road Cycling | La Flèche Wallonne | Classics | Men | Marcel Kint | Belgium | 1 |
| 1944 | Road Cycling | La Flèche Wallonne | Classics | Men | Marcel Kint | Belgium | 1 |
| 1943 | Road Cycling | La Flèche Wallonne | Classics | Men | Marcel Kint | Belgium | 1 |
| 1942 | Road Cycling | La Flèche Wallonne | Classics | Men | Karel Thijs | Belgium | 1 |
| 1941 | Road Cycling | La Flèche Wallonne | Classics | Men | Sylvain Grysolle | Belgium | 1 |
| 1939 | Road Cycling | La Flèche Wallonne | Classics | Men | Edmond Delathouwer | Belgium | 1 |
| 1938 | Road Cycling | La Flèche Wallonne | Classics | Men | Émile Masson | Belgium | 1 |
| 1937 | Road Cycling | La Flèche Wallonne | Classics | Men | Adolf Braeckeveldt | Belgium | 1 |
| 1936 | Road Cycling | La Flèche Wallonne | Classics | Men | Philémon De Meersman | Belgium | 1 |
| 2025 | Road Cycling | Giro de Italia | Young jersey | Men | Isaac del Toro | Mexico | 1 |
| 2024 | Road Cycling | Giro de Italia | Young jersey | Men | Antonio Tiberi | Italy | 1 |
| 2023 | Road Cycling | Giro de Italia | Young jersey | Men | João Almeida | Portugal | 1 |
| 2022 | Road Cycling | Giro de Italia | Young jersey | Men | Juan Pedro López Pérez | Spain | 1 |
| 2021 | Road Cycling | Giro de Italia | Young jersey | Men | Egan Bernal | Colombia | 1 |
| 2020 | Road Cycling | Giro de Italia | Young jersey | Men | Tao Geoghegan Hart | Great Britain | 1 |
| 2019 | Road Cycling | Giro de Italia | Young jersey | Men | Miguel Ángel López | Colombia | 1 |
| 2018 | Road Cycling | Giro de Italia | Young jersey | Men | Miguel Ángel López | Colombia | 1 |
| 2017 | Road Cycling | Giro de Italia | Young jersey | Men | Bob Jungels | Luxembourg | 1 |
| 2016 | Road Cycling | Giro de Italia | Young jersey | Men | Bob Jungels | Luxembourg | 1 |
| 2015 | Road Cycling | Giro de Italia | Young jersey | Men | Fabio Aru | Italy | 1 |
| 2014 | Road Cycling | Giro de Italia | Young jersey | Men | Nairo Quintana | Colombia | 1 |
| 2013 | Road Cycling | Giro de Italia | Young jersey | Men | Carlos Betancur | Colombia | 1 |
| 2012 | Road Cycling | Giro de Italia | Young jersey | Men | Rigoberto Urán | Colombia | 1 |
| 2011 | Road Cycling | Giro de Italia | Young jersey | Men | Roman Kreuziger | Czech Republic | 1 |
| 2010 | Road Cycling | Giro de Italia | Young jersey | Men | Richie Porte | Australia | 1 |
| 2009 | Road Cycling | Giro de Italia | Young jersey | Men | Kevin Seeldraeyers | Belgium | 1 |
| 2008 | Road Cycling | Giro de Italia | Young jersey | Men | Riccardo Riccò | Italy | 1 |
| 2007 | Road Cycling | Giro de Italia | Young jersey | Men | Andy Schleck | Luxembourg | 1 |
| 1994 | Road Cycling | Giro de Italia | Young jersey | Men | Evgeni Berzin | Russia | 1 |
| 1993 | Road Cycling | Giro de Italia | Young jersey | Men | Pavel Tonkov | Russia | 1 |
| 1992 | Road Cycling | Giro de Italia | Young jersey | Men | Pavel Tonkov | Russia | 1 |
| 1991 | Road Cycling | Giro de Italia | Young jersey | Men | Massimiliano Lelli | Italy | 1 |
| 1990 | Road Cycling | Giro de Italia | Young jersey | Men | Vladimir Poulnikov | Soviet Union | 1 |
| 1989 | Road Cycling | Giro de Italia | Young jersey | Men | Vladimir Poulnikov | Soviet Union | 1 |
| 1988 | Road Cycling | Giro de Italia | Young jersey | Men | Stefano Tomasini | Italy | 1 |
| 1987 | Road Cycling | Giro de Italia | Young jersey | Men | Roberto Conti | Italy | 1 |
| 1986 | Road Cycling | Giro de Italia | Young jersey | Men | Marco Giovannetti | Italy | 1 |
| 1985 | Road Cycling | Giro de Italia | Young jersey | Men | Alberto Volpi | Italy | 1 |
| 1984 | Road Cycling | Giro de Italia | Young jersey | Men | Charly Mottet | France | 1 |
| 1983 | Road Cycling | Giro de Italia | Young jersey | Men | Franco Chioccioli | Italy | 1 |
| 1982 | Road Cycling | Giro de Italia | Young jersey | Men | Marco Groppo | Italy | 1 |
| 1981 | Road Cycling | Giro de Italia | Young jersey | Men | Giuseppe Faraca | Italy | 1 |
| 1980 | Road Cycling | Giro de Italia | Young jersey | Men | Tommy Prim | Sweden | 1 |
| 1979 | Road Cycling | Giro de Italia | Young jersey | Men | Silvano Contini | Italy | 1 |
| 1978 | Road Cycling | Giro de Italia | Young jersey | Men | Roberto Visentini | Italy | 1 |
| 1977 | Road Cycling | Giro de Italia | Young jersey | Men | Mario Beccia | Italy | 1 |
| 1976 | Road Cycling | Giro de Italia | Young jersey | Men | Alfio Vandi | Italy | 1 |
| 2025 | Road Cycling | Giro de Italia | Sprint jersey | Men | Mads Pedersen | Denmark | 1 |
| 2024 | Road Cycling | Giro de Italia | Sprint jersey | Men | Jonathan Milan | Italy | 1 |
| 2023 | Road Cycling | Giro de Italia | Sprint jersey | Men | Jonathan Milan | Italy | 1 |
| 2022 | Road Cycling | Giro de Italia | Sprint jersey | Men | Arnaud Démare | France | 1 |
| 2021 | Road Cycling | Giro de Italia | Sprint jersey | Men | Peter Sagan | Slovakia | 1 |
| 2020 | Road Cycling | Giro de Italia | Sprint jersey | Men | Arnaud Démare | France | 1 |
| 2019 | Road Cycling | Giro de Italia | Sprint jersey | Men | Pascal Ackermann | Germany | 1 |
| 2018 | Road Cycling | Giro de Italia | Sprint jersey | Men | Elia Viviani | Italy | 1 |
| 2017 | Road Cycling | Giro de Italia | Sprint jersey | Men | Fernando Gaviria | Colombia | 1 |
| 2016 | Road Cycling | Giro de Italia | Sprint jersey | Men | Giacomo Nizzolo | Italy | 1 |
| 2015 | Road Cycling | Giro de Italia | Sprint jersey | Men | Giacomo Nizzolo | Italy | 1 |
| 2014 | Road Cycling | Giro de Italia | Sprint jersey | Men | Nacer Bouhanni | France | 1 |
| 2013 | Road Cycling | Giro de Italia | Sprint jersey | Men | Mark Cavendish | Great Britain | 1 |
| 2012 | Road Cycling | Giro de Italia | Sprint jersey | Men | Joaquim Rodríguez | Spain | 1 |
| 2011 | Road Cycling | Giro de Italia | Sprint jersey | Men | Michele Scarponi | Italy | 1 |
| 2010 | Road Cycling | Giro de Italia | Sprint jersey | Men | Cadel Evans | Australia | 1 |
| 2009 | Road Cycling | Giro de Italia | Sprint jersey | Men | Denis Menchov | Russia | 1 |
| 2008 | Road Cycling | Giro de Italia | Sprint jersey | Men | Daniele Bennati | Italy | 1 |
| 2006 | Road Cycling | Giro de Italia | Sprint jersey | Men | Paolo Bettini | Italy | 1 |
| 2005 | Road Cycling | Giro de Italia | Sprint jersey | Men | Paolo Bettini | Italy | 1 |
| 2004 | Road Cycling | Giro de Italia | Sprint jersey | Men | Alessandro Petacchi | Italy | 1 |
| 2003 | Road Cycling | Giro de Italia | Sprint jersey | Men | Gilberto Simoni | Italy | 1 |
| 2002 | Road Cycling | Giro de Italia | Sprint jersey | Men | Mario Cipollini | Italy | 1 |
| 2001 | Road Cycling | Giro de Italia | Sprint jersey | Men | Massimo Strazzer | Italy | 1 |
| 2000 | Road Cycling | Giro de Italia | Sprint jersey | Men | Dimitri Konychev | Russia | 1 |
| 1999 | Road Cycling | Giro de Italia | Sprint jersey | Men | Laurent Jalabert | France | 1 |
| 1998 | Road Cycling | Giro de Italia | Sprint jersey | Men | Mariano Piccoli | Italy | 1 |
| 1997 | Road Cycling | Giro de Italia | Sprint jersey | Men | Mario Cipollini | Italy | 1 |
| 1996 | Road Cycling | Giro de Italia | Sprint jersey | Men | Fabrizio Guidi | Italy | 1 |
| 1995 | Road Cycling | Giro de Italia | Sprint jersey | Men | Tony Rominger | Switzerland | 1 |
| 1994 | Road Cycling | Giro de Italia | Sprint jersey | Men | Djamolidine Abdoujaparov | Russia | 1 |
| 1993 | Road Cycling | Giro de Italia | Sprint jersey | Men | Adriano Baffi | Italy | 1 |
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