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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1906 | Road Cycling | Tour de France | Mountain jersey | Men | René Pottier | France | 1 |
| 1905 | Road Cycling | Tour de France | Mountain jersey | Men | René Pottier | France | 1 |
| 2025 | Road Cycling | Tour de France | Young jersey | Men | Florian Lipowitz | Germany | 1 |
| 2024 | Road Cycling | Tour de France | Young jersey | Men | Remco Evenepoel | Belgium | 1 |
| 2023 | Road Cycling | Tour de France | Young jersey | Men | Tadej Pogačar | Slovenia | 1 |
| 2022 | Road Cycling | Tour de France | Young jersey | Men | Tadej Pogačar | Slovenia | 1 |
| 2021 | Road Cycling | Tour de France | Young jersey | Men | Tadej Pogačar | Slovenia | 1 |
| 2020 | Road Cycling | Tour de France | Young jersey | Men | Tadej Pogačar | Slovenia | 1 |
| 2019 | Road Cycling | Tour de France | Young jersey | Men | Egan Bernal | Colombia | 1 |
| 2018 | Road Cycling | Tour de France | Young jersey | Men | Pierre Latour | France | 1 |
| 2017 | Road Cycling | Tour de France | Young jersey | Men | Simon Yates | Great Britain | 1 |
| 2016 | Road Cycling | Tour de France | Young jersey | Men | Adam Yates | Great Britain | 1 |
| 2015 | Road Cycling | Tour de France | Young jersey | Men | Nairo Quintana | Colombia | 1 |
| 2014 | Road Cycling | Tour de France | Young jersey | Men | Thibaut Pinot | France | 1 |
| 2013 | Road Cycling | Tour de France | Young jersey | Men | Nairo Quintana | Colombia | 1 |
| 2012 | Road Cycling | Tour de France | Young jersey | Men | Tejay van Garderen | United States | 1 |
| 2011 | Road Cycling | Tour de France | Young jersey | Men | Pierre Rolland | France | 1 |
| 2010 | Road Cycling | Tour de France | Young jersey | Men | Andy Schleck | Luxembourg | 1 |
| 2009 | Road Cycling | Tour de France | Young jersey | Men | Andy Schleck | Luxembourg | 1 |
| 2008 | Road Cycling | Tour de France | Young jersey | Men | Andy Schleck | Luxembourg | 1 |
| 2007 | Road Cycling | Tour de France | Young jersey | Men | Alberto Contador | Spain | 1 |
| 2006 | Road Cycling | Tour de France | Young jersey | Men | Damiano Cunego | Italy | 1 |
| 2005 | Road Cycling | Tour de France | Young jersey | Men | Yaroslav Popovych | Ukraine | 1 |
| 2004 | Road Cycling | Tour de France | Young jersey | Men | Vladimir Karpets | Russia | 1 |
| 2003 | Road Cycling | Tour de France | Young jersey | Men | Denis Menchov | Russia | 1 |
| 2002 | Road Cycling | Tour de France | Young jersey | Men | Ivan Basso | Italy | 1 |
| 2001 | Road Cycling | Tour de France | Young jersey | Men | Óscar Sevilla | Spain | 1 |
| 2000 | Road Cycling | Tour de France | Young jersey | Men | Francisco Mancebo | Spain | 1 |
| 1999 | Road Cycling | Tour de France | Young jersey | Men | Benoît Salmon | France | 1 |
| 1998 | Road Cycling | Tour de France | Young jersey | Men | Jan Ullrich | Germany | 1 |
| 1997 | Road Cycling | Tour de France | Young jersey | Men | Jan Ullrich | Germany | 1 |
| 1996 | Road Cycling | Tour de France | Young jersey | Men | Jan Ullrich | Germany | 1 |
| 1995 | Road Cycling | Tour de France | Young jersey | Men | Marco Pantani | Italy | 1 |
| 1994 | Road Cycling | Tour de France | Young jersey | Men | Marco Pantani | Italy | 1 |
| 1993 | Road Cycling | Tour de France | Young jersey | Men | Antonio Martín | Spain | 1 |
| 1992 | Road Cycling | Tour de France | Young jersey | Men | Eddy Bouwmans | Netherlands | 1 |
| 1991 | Road Cycling | Tour de France | Young jersey | Men | Álvaro Mejía | Colombia | 1 |
| 1990 | Road Cycling | Tour de France | Young jersey | Men | Gilles Delion | France | 1 |
| 1989 | Road Cycling | Tour de France | Young jersey | Men | Fabrice Philipot | France | 1 |
| 1988 | Road Cycling | Tour de France | Young jersey | Men | Erik Breukink | Netherlands | 1 |
| 1987 | Road Cycling | Tour de France | Young jersey | Men | Raúl Alcalá | Mexico | 1 |
| 1986 | Road Cycling | Tour de France | Young jersey | Men | Andrew Hampsten | United States | 1 |
| 1985 | Road Cycling | Tour de France | Young jersey | Men | Fabio Parra | Colombia | 1 |
| 1984 | Road Cycling | Tour de France | Young jersey | Men | Greg LeMond | United States | 1 |
| 1983 | Road Cycling | Tour de France | Young jersey | Men | Laurent Fignon | France | 1 |
| 1982 | Road Cycling | Tour de France | Young jersey | Men | Phil Anderson | Australia | 1 |
| 1981 | Road Cycling | Tour de France | Young jersey | Men | Peter Winnen | Netherlands | 1 |
| 1980 | Road Cycling | Tour de France | Young jersey | Men | Johan van der Velde | Netherlands | 1 |
| 1979 | Road Cycling | Tour de France | Young jersey | Men | Jean-René Bernaudeau | France | 1 |
| 1978 | Road Cycling | Tour de France | Young jersey | Men | Henk Lubberding | Netherlands | 1 |
| 1977 | Road Cycling | Tour de France | Young jersey | Men | Dietrich Thurau | West Germany | 1 |
| 1976 | Road Cycling | Tour de France | Young jersey | Men | Enrique Martínez Heredia | Spain | 1 |
| 1975 | Road Cycling | Tour de France | Young jersey | Men | Francesco Moser | Italy | 1 |
| 2025 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Juan Ayuso | Spain | 1 |
| 2024 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Jonas Vingegaard | Denmark | 1 |
| 2023 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Primož Roglič | Slovenia | 1 |
| 2022 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Tadej Pogačar | Slovenia | 1 |
| 2021 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Tadej Pogačar | Slovenia | 1 |
| 2020 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Simon Yates | Great Britain | 1 |
| 2019 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Primož Roglič | Slovenia | 1 |
| 2018 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Michał Kwiatkowski | Poland | 1 |
| 2017 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Nairo Quintana | Colombia | 1 |
| 2016 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Greg Van Avermaet | Belgium | 1 |
| 2015 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Nairo Quintana | Colombia | 1 |
| 2014 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Alberto Contador | Spain | 1 |
| 2013 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Vincenzo Nibali | Italy | 1 |
| 2012 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Vincenzo Nibali | Italy | 1 |
| 2011 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Cadel Evans | Australia | 1 |
| 2010 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Stefano Garzelli | Italy | 1 |
| 2009 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Michele Scarponi | Italy | 1 |
| 2008 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Fabian Cancellara | Switzerland | 1 |
| 2007 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Andreas Klöden | Germany | 1 |
| 2006 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Thomas Dekker | Netherlands | 1 |
| 2005 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Óscar Freire | Spain | 1 |
| 2004 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Paolo Bettini | Italy | 1 |
| 2003 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Filippo Pozzato | Italy | 1 |
| 2002 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Erik Dekker | Netherlands | 1 |
| 2001 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Davide Rebellin | Italy | 1 |
| 2000 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Abraham Olano | Spain | 1 |
| 1999 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Michele Bartoli | Italy | 1 |
| 1998 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Rolf Järmann | Switzerland | 1 |
| 1997 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Roberto Petito | Italy | 1 |
| 1996 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Francesco Casagrande | Italy | 1 |
| 1995 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Stefano Colagé | Italy | 1 |
| 1994 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Giorgio Furlan | Italy | 1 |
| 1993 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Maurizio Fondriest | Italy | 1 |
| 1992 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Rolf Sørensen | Denmark | 1 |
| 1991 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Herminio Díaz-Zabala | Spain | 1 |
| 1990 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Tony Rominger | Switzerland | 1 |
| 1989 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Tony Rominger | Switzerland | 1 |
| 1988 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Erich Mächler | Switzerland | 1 |
| 1987 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Rolf Sørensen | Denmark | 1 |
| 1986 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Luciano Rabottini | Italy | 1 |
| 1985 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Joop Zoetemelk | Netherlands | 1 |
| 1984 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Tommy Prim | Sweden | 1 |
| 1983 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Roberto Visentini | Italy | 1 |
| 1982 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Giuseppe Saronni | Italy | 1 |
| 1981 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Francesco Moser | Italy | 1 |
| 1980 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Francesco Moser | Italy | 1 |
| 1979 | Road Cycling | Tirreno–Adriatico | Stage race | Men | Knut Knudsen | Norway | 1 |
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