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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1923 | Road Cycling | Tour de France | Mountain jersey | Men | Henri Pélissier | France | 1 |
| 2008 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 1986 | Road Cycling | Giro de Italia | Mountain jersey | Men | Pedro Muñoz | Spain | 1 |
| 1924 | Road Cycling | Tour de France | Mountain jersey | Men | Ottavio Bottecchia | Italy | 1 |
| 2009 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 1987 | Road Cycling | Giro de Italia | Mountain jersey | Men | Robert Millar | Great Britain | 1 |
| 1925 | Road Cycling | Tour de France | Mountain jersey | Men | Ottavio Bottecchia | Italy | 1 |
| 2010 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 1988 | Road Cycling | Giro de Italia | Mountain jersey | Men | Andrew Hampsten | United States | 1 |
| 1926 | Road Cycling | Tour de France | Mountain jersey | Men | Lucien Buysse | Belgium | 1 |
| 2011 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 1989 | Road Cycling | Giro de Italia | Mountain jersey | Men | Luis Herrera | Colombia | 1 |
| 1927 | Road Cycling | Tour de France | Mountain jersey | Men | Giovanni-Michele Gordini | Italy | 1 |
| 2012 | Road Cycling | Vuelta a España | Mountain jersey | Men | Simon Clarke | Australia | 1 |
| 1990 | Road Cycling | Giro de Italia | Mountain jersey | Men | Claudio Chiappucci | Italy | 1 |
| 1928 | Road Cycling | Tour de France | Mountain jersey | Men | Victor Fontan | France | 1 |
| 2013 | Road Cycling | Vuelta a España | Mountain jersey | Men | Nicolas Edet | France | 1 |
| 1991 | Road Cycling | Giro de Italia | Mountain jersey | Men | Iñaki Gastón Crespo | Spain | 1 |
| 1929 | Road Cycling | Tour de France | Mountain jersey | Men | Victor Fontan | France | 1 |
| 2014 | Road Cycling | Vuelta a España | Mountain jersey | Men | Luis León Sánchez | Spain | 1 |
| 1992 | Road Cycling | Giro de Italia | Mountain jersey | Men | Claudio Chiappucci | Italy | 1 |
| 1930 | Road Cycling | Tour de France | Mountain jersey | Men | Benoît Fauré | France | 1 |
| 2015 | Road Cycling | Vuelta a España | Mountain jersey | Men | Omar Fraile | Spain | 1 |
| 1993 | Road Cycling | Giro de Italia | Mountain jersey | Men | Claudio Chiappucci | Italy | 1 |
| 1931 | Road Cycling | Tour de France | Mountain jersey | Men | Joseph Demuysere | Belgium | 1 |
| 2016 | Road Cycling | Vuelta a España | Mountain jersey | Men | Omar Fraile | Spain | 1 |
| 1994 | Road Cycling | Giro de Italia | Mountain jersey | Men | Pascal Richard | Switzerland | 1 |
| 1932 | Road Cycling | Tour de France | Mountain jersey | Men | Vicente Trueba | Spain | 1 |
| 2017 | Road Cycling | Vuelta a España | Mountain jersey | Men | Davide Villella | Italy | 1 |
| 1995 | Road Cycling | Giro de Italia | Mountain jersey | Men | Mariano Piccoli | Italy | 1 |
| 1933 | Road Cycling | Tour de France | Mountain jersey | Men | Vicente Trueba | Spain | 1 |
| 2018 | Road Cycling | Vuelta a España | Mountain jersey | Men | Thomas De Gendt | Belgium | 1 |
| 1996 | Road Cycling | Giro de Italia | Mountain jersey | Men | Mariano Piccoli | Italy | 1 |
| 1934 | Road Cycling | Tour de France | Mountain jersey | Men | René Vietto | France | 1 |
| 2019 | Road Cycling | Vuelta a España | Mountain jersey | Men | Geoffrey Bouchard | France | 1 |
| 1997 | Road Cycling | Giro de Italia | Mountain jersey | Men | Chepe González | Colombia | 1 |
| 1935 | Road Cycling | Tour de France | Mountain jersey | Men | Félicien Vervaecke | Belgium | 1 |
| 2020 | Road Cycling | Vuelta a España | Mountain jersey | Men | Guillaume Martin | France | 1 |
| 1998 | Road Cycling | Giro de Italia | Mountain jersey | Men | Marco Pantani | Italy | 1 |
| 1936 | Road Cycling | Tour de France | Mountain jersey | Men | Julián Berrendero | Spain | 1 |
| 2021 | Road Cycling | Vuelta a España | Mountain jersey | Men | Michael Storer | Australia | 1 |
| 1999 | Road Cycling | Giro de Italia | Mountain jersey | Men | Chepe González | Colombia | 1 |
| 1937 | Road Cycling | Tour de France | Mountain jersey | Men | Félicien Vervaecke | Belgium | 1 |
| 2022 | Road Cycling | Vuelta a España | Mountain jersey | Men | Richard Carapaz | Ecuador | 1 |
| 2000 | Road Cycling | Giro de Italia | Mountain jersey | Men | Francesco Casagrande | Italy | 1 |
| 1938 | Road Cycling | Tour de France | Mountain jersey | Men | Gino Bartali | Italy | 1 |
| 2023 | Road Cycling | Vuelta a España | Mountain jersey | Men | Remco Evenepoel | Belgium | 1 |
| 2001 | Road Cycling | Giro de Italia | Mountain jersey | Men | Fredy González | Colombia | 1 |
| 1939 | Road Cycling | Tour de France | Mountain jersey | Men | Sylvère Maes | Belgium | 1 |
| 2024 | Road Cycling | Vuelta a España | Mountain jersey | Men | Jay Vine | Australia | 1 |
| 2002 | Road Cycling | Giro de Italia | Mountain jersey | Men | Julio Alberto Pérez | Mexico | 1 |
| 1947 | Road Cycling | Tour de France | Mountain jersey | Men | Pierre Brambilla | France | 1 |
| 2025 | Road Cycling | Vuelta a España | Mountain jersey | Men | Jay Vine | Australia | 1 |
| 2003 | Road Cycling | Giro de Italia | Mountain jersey | Men | Fredy González | Colombia | 1 |
| 1948 | Road Cycling | Tour de France | Mountain jersey | Men | Gino Bartali | Italy | 1 |
| 2004 | Road Cycling | Giro de Italia | Mountain jersey | Men | Fabian Wegmann | Germany | 1 |
| 1949 | Road Cycling | Tour de France | Mountain jersey | Men | Fausto Coppi | Italy | 1 |
| 2005 | Road Cycling | Giro de Italia | Mountain jersey | Men | José Rujano Guillen | Venezuela | 1 |
| 1950 | Road Cycling | Tour de France | Mountain jersey | Men | Louison Bobet | France | 1 |
| 2006 | Road Cycling | Giro de Italia | Mountain jersey | Men | Juan Manuel Gárate | Spain | 1 |
| 1951 | Road Cycling | Tour de France | Mountain jersey | Men | Raphael Géminiani | France | 1 |
| 2007 | Road Cycling | Giro de Italia | Mountain jersey | Men | Leonardo Piepoli | Italy | 1 |
| 1952 | Road Cycling | Tour de France | Mountain jersey | Men | Fausto Coppi | Italy | 1 |
| 2008 | Road Cycling | Giro de Italia | Mountain jersey | Men | Emanuele Sella | Italy | 1 |
| 1953 | Road Cycling | Tour de France | Mountain jersey | Men | Jesús Loroño | Spain | 1 |
| 2009 | Road Cycling | Giro de Italia | Mountain jersey | Men | Stefano Garzelli | Italy | 1 |
| 1954 | Road Cycling | Tour de France | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 2010 | Road Cycling | Giro de Italia | Mountain jersey | Men | Matthew Lloyd | Australia | 1 |
| 1955 | Road Cycling | Tour de France | Mountain jersey | Men | Charly Gaul | Luxembourg | 1 |
| 2011 | Road Cycling | Giro de Italia | Mountain jersey | Men | Stefano Garzelli | Italy | 1 |
| 1956 | Road Cycling | Tour de France | Mountain jersey | Men | Charly Gaul | Luxembourg | 1 |
| 2012 | Road Cycling | Giro de Italia | Mountain jersey | Men | Matteo Rabottini | Italy | 1 |
| 1957 | Road Cycling | Tour de France | Mountain jersey | Men | Gastone Nencini | Italy | 1 |
| 2013 | Road Cycling | Giro de Italia | Mountain jersey | Men | Stefano Pirazzi | Italy | 1 |
| 1958 | Road Cycling | Tour de France | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 2014 | Road Cycling | Giro de Italia | Mountain jersey | Men | Julián Arredondo | Colombia | 1 |
| 1959 | Road Cycling | Tour de France | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 2015 | Road Cycling | Giro de Italia | Mountain jersey | Men | Giovanni Visconti | Italy | 1 |
| 1960 | Road Cycling | Tour de France | Mountain jersey | Men | Imerio Massignan | Italy | 1 |
| 2016 | Road Cycling | Giro de Italia | Mountain jersey | Men | Mikel Nieve | Spain | 1 |
| 1961 | Road Cycling | Tour de France | Mountain jersey | Men | Imerio Massignan | Italy | 1 |
| 2017 | Road Cycling | Giro de Italia | Mountain jersey | Men | Mikel Landa | Spain | 1 |
| 1962 | Road Cycling | Tour de France | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 2018 | Road Cycling | Giro de Italia | Mountain jersey | Men | Chris Froome | Great Britain | 1 |
| 1963 | Road Cycling | Tour de France | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 2019 | Road Cycling | Giro de Italia | Mountain jersey | Men | Giulio Ciccone | Italy | 1 |
| 1964 | Road Cycling | Tour de France | Mountain jersey | Men | Federico Bahamontes | Spain | 1 |
| 2020 | Road Cycling | Giro de Italia | Mountain jersey | Men | Ruben Guerreiro | Portugal | 1 |
| 1965 | Road Cycling | Tour de France | Mountain jersey | Men | Julio Jimenez | Spain | 1 |
| 2021 | Road Cycling | Giro de Italia | Mountain jersey | Men | Geoffrey Bouchard | France | 1 |
| 1966 | Road Cycling | Tour de France | Mountain jersey | Men | Julio Jimenez | Spain | 1 |
| 2022 | Road Cycling | Giro de Italia | Mountain jersey | Men | Koen Bouwman | Netherlands | 1 |
| 1967 | Road Cycling | Tour de France | Mountain jersey | Men | Julio Jimenez | Spain | 1 |
| 2023 | Road Cycling | Giro de Italia | Mountain jersey | Men | Thibaut Pinot | France | 1 |
| 1968 | Road Cycling | Tour de France | Mountain jersey | Men | Aurelio González | Spain | 1 |
| 2024 | Road Cycling | Giro de Italia | Mountain jersey | Men | Tadej Pogačar | Slovenia | 1 |
| 1969 | Road Cycling | Tour de France | Mountain jersey | Men | Eddy Merckx | Belgium | 1 |
| 2025 | Road Cycling | Giro de Italia | Mountain jersey | Men | Lorenzo Fortunato | Italy | 1 |
| 1970 | Road Cycling | Tour de France | Mountain jersey | Men | Eddy Merckx | Belgium | 1 |
| 1971 | Road Cycling | Tour de France | Mountain jersey | Men | Lucien Van Impe | Belgium | 1 |
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