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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1965 | Road Cycling | Vuelta a España | Mountain jersey | Men | Julio Jimenez | Spain | 1 |
| 1939 | Road Cycling | Giro de Italia | Mountain jersey | Men | Gino Bartali | Italy | 1 |
| 1966 | Road Cycling | Vuelta a España | Mountain jersey | Men | Gregorio San Miguel | Spain | 1 |
| 1940 | Road Cycling | Giro de Italia | Mountain jersey | Men | Gino Bartali | Italy | 1 |
| 1967 | Road Cycling | Vuelta a España | Mountain jersey | Men | Mariano Díaz | Spain | 1 |
| 1946 | Road Cycling | Giro de Italia | Mountain jersey | Men | Gino Bartali | Italy | 1 |
| 1968 | Road Cycling | Vuelta a España | Mountain jersey | Men | Francisco Gabica | Spain | 1 |
| 1947 | Road Cycling | Giro de Italia | Mountain jersey | Men | Gino Bartali | Italy | 1 |
| 1969 | Road Cycling | Vuelta a España | Mountain jersey | Men | Luis Ocaña | Spain | 1 |
| 1948 | Road Cycling | Giro de Italia | Mountain jersey | Men | Fausto Coppi | Italy | 1 |
| 1970 | Road Cycling | Vuelta a España | Mountain jersey | Men | Agustín Tamames | Spain | 1 |
| 1949 | Road Cycling | Giro de Italia | Mountain jersey | Men | Fausto Coppi | Italy | 1 |
| 1971 | Road Cycling | Vuelta a España | Mountain jersey | Men | Joop Zoetemelk | Netherlands | 1 |
| 1950 | Road Cycling | Giro de Italia | Mountain jersey | Men | Hugo Koblet | Switzerland | 1 |
| 1972 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Manuel Fuente | Spain | 1 |
| 1951 | Road Cycling | Giro de Italia | Mountain jersey | Men | Louison Bobet | France | 1 |
| 1973 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Abilleira | Spain | 1 |
| 1952 | Road Cycling | Giro de Italia | Mountain jersey | Men | Raphael Géminiani | France | 1 |
| 1974 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Abilleira | Spain | 1 |
| 1953 | Road Cycling | Giro de Italia | Mountain jersey | Men | Pasquale Fornara | Italy | 1 |
| 1975 | Road Cycling | Vuelta a España | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1954 | Road Cycling | Giro de Italia | Mountain jersey | Men | Fausto Coppi | Italy | 1 |
| 1976 | Road Cycling | Vuelta a España | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1955 | Road Cycling | Giro de Italia | Mountain jersey | Men | Gastone Nencini | Italy | 1 |
| 1977 | Road Cycling | Vuelta a España | Mountain jersey | Men | Pedro Torres | Spain | 1 |
| 1956 | Road Cycling | Giro de Italia | Mountain jersey | Men | Charly Gaul | Luxembourg | 1 |
| 1978 | Road Cycling | Vuelta a España | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1957 | Road Cycling | Giro de Italia | Mountain jersey | Men | Raphael Géminiani | France | 1 |
| 1979 | Road Cycling | Vuelta a España | Mountain jersey | Men | Felipe Yáñez | Spain | 1 |
| 1958 | Road Cycling | Giro de Italia | Mountain jersey | Men | Jean Brankart | Belgium | 1 |
| 1980 | Road Cycling | Vuelta a España | Mountain jersey | Men | Juan Fernández | Spain | 1 |
| 1959 | Road Cycling | Giro de Italia | Mountain jersey | Men | Charly Gaul | Luxembourg | 1 |
| 1981 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1960 | Road Cycling | Giro de Italia | Mountain jersey | Men | Rik Van Looy | Belgium | 1 |
| 1982 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1961 | Road Cycling | Giro de Italia | Mountain jersey | Men | Vito Taccone | Italy | 1 |
| 1983 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1962 | Road Cycling | Giro de Italia | Mountain jersey | Men | Angelino Soler | Spain | 1 |
| 1984 | Road Cycling | Vuelta a España | Mountain jersey | Men | Felipe Yáñez | Spain | 1 |
| 1963 | Road Cycling | Giro de Italia | Mountain jersey | Men | Vito Taccone | Italy | 1 |
| 1985 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1964 | Road Cycling | Giro de Italia | Mountain jersey | Men | Franco Bitossi | Italy | 1 |
| 1986 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1965 | Road Cycling | Giro de Italia | Mountain jersey | Men | Franco Bitossi | Italy | 1 |
| 1987 | Road Cycling | Vuelta a España | Mountain jersey | Men | Lucho Herrera | Colombia | 1 |
| 1966 | Road Cycling | Giro de Italia | Mountain jersey | Men | Franco Bitossi | Italy | 1 |
| 1988 | Road Cycling | Vuelta a España | Mountain jersey | Men | Álvaro Pino | Spain | 1 |
| 1967 | Road Cycling | Giro de Italia | Mountain jersey | Men | Aurelio González | Spain | 1 |
| 1989 | Road Cycling | Vuelta a España | Mountain jersey | Men | Óscar Vargas | Colombia | 1 |
| 1968 | Road Cycling | Giro de Italia | Mountain jersey | Men | Eddy Merckx | Belgium | 1 |
| 1990 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Martín Farfán | Colombia | 1 |
| 1969 | Road Cycling | Giro de Italia | Mountain jersey | Men | Claudio Michelotto | Italy | 1 |
| 1991 | Road Cycling | Vuelta a España | Mountain jersey | Men | Lucho Herrera | Colombia | 1 |
| 1970 | Road Cycling | Giro de Italia | Mountain jersey | Men | Martin Van Den Bossche | Belgium | 1 |
| 1992 | Road Cycling | Vuelta a España | Mountain jersey | Men | Carlos Hernández | Spain | 1 |
| 1971 | Road Cycling | Giro de Italia | Mountain jersey | Men | José Manuel Fuente | Spain | 1 |
| 1993 | Road Cycling | Vuelta a España | Mountain jersey | Men | Tony Rominger | Switzerland | 1 |
| 1972 | Road Cycling | Giro de Italia | Mountain jersey | Men | José Manuel Fuente | Spain | 1 |
| 1905 | Road Cycling | Tour de France | Mountain jersey | Men | René Pottier | France | 1 |
| 1994 | Road Cycling | Vuelta a España | Mountain jersey | Men | Luc Leblanc | France | 1 |
| 1973 | Road Cycling | Giro de Italia | Mountain jersey | Men | José Manuel Fuente | Spain | 1 |
| 1906 | Road Cycling | Tour de France | Mountain jersey | Men | René Pottier | France | 1 |
| 1995 | Road Cycling | Vuelta a España | Mountain jersey | Men | Laurent Jalabert | France | 1 |
| 1974 | Road Cycling | Giro de Italia | Mountain jersey | Men | José Manuel Fuente | Spain | 1 |
| 1907 | Road Cycling | Tour de France | Mountain jersey | Men | Emile Georget | France | 1 |
| 1996 | Road Cycling | Vuelta a España | Mountain jersey | Men | Tony Rominger | Switzerland | 1 |
| 1975 | Road Cycling | Giro de Italia | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1908 | Road Cycling | Tour de France | Mountain jersey | Men | Gustave Garrigou | France | 1 |
| 1997 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 1975 | Road Cycling | Giro de Italia | Mountain jersey | Men | Francisco Galdós | Spain | 1 |
| 1909 | Road Cycling | Tour de France | Mountain jersey | Men | François Faber | Luxembourg | 1 |
| 1998 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 1976 | Road Cycling | Giro de Italia | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1910 | Road Cycling | Tour de France | Mountain jersey | Men | Octave Lapize | France | 1 |
| 1999 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 1977 | Road Cycling | Giro de Italia | Mountain jersey | Men | Faustino Fernández Ovies | Spain | 1 |
| 1911 | Road Cycling | Tour de France | Mountain jersey | Men | Paul Duboc | France | 1 |
| 2000 | Road Cycling | Vuelta a España | Mountain jersey | Men | Carlos Sastre | Spain | 1 |
| 1978 | Road Cycling | Giro de Italia | Mountain jersey | Men | Ueli Sutter | Switzerland | 1 |
| 1912 | Road Cycling | Tour de France | Mountain jersey | Men | Odile Defraye | Belgium | 1 |
| 2001 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 1979 | Road Cycling | Giro de Italia | Mountain jersey | Men | Claudio Bortolotto | Italy | 1 |
| 1913 | Road Cycling | Tour de France | Mountain jersey | Men | Philippe Thys | Belgium | 1 |
| 2002 | Road Cycling | Vuelta a España | Mountain jersey | Men | Aitor Osa | Spain | 1 |
| 1980 | Road Cycling | Giro de Italia | Mountain jersey | Men | Claudio Bortolotto | Italy | 1 |
| 1914 | Road Cycling | Tour de France | Mountain jersey | Men | Firmin Lambot | Belgium | 1 |
| 2003 | Road Cycling | Vuelta a España | Mountain jersey | Men | Félix Cárdenas | Colombia | 1 |
| 1981 | Road Cycling | Giro de Italia | Mountain jersey | Men | Claudio Bortolotto | Italy | 1 |
| 1919 | Road Cycling | Tour de France | Mountain jersey | Men | Honoré Barthelemy | France | 1 |
| 2004 | Road Cycling | Vuelta a España | Mountain jersey | Men | Félix Cárdenas | Colombia | 1 |
| 1982 | Road Cycling | Giro de Italia | Mountain jersey | Men | Lucien Van Impe | Belgium | 1 |
| 1920 | Road Cycling | Tour de France | Mountain jersey | Men | Firmin Lambot | Belgium | 1 |
| 2005 | Road Cycling | Vuelta a España | Mountain jersey | Men | Joaquim Rodríguez | Spain | 1 |
| 1983 | Road Cycling | Giro de Italia | Mountain jersey | Men | Lucien Van Impe | Belgium | 1 |
| 1921 | Road Cycling | Tour de France | Mountain jersey | Men | Hector Heusghem | Belgium | 1 |
| 2006 | Road Cycling | Vuelta a España | Mountain jersey | Men | Egoi Martínez | Spain | 1 |
| 1984 | Road Cycling | Giro de Italia | Mountain jersey | Men | Laurent Fignon | France | 1 |
| 1922 | Road Cycling | Tour de France | Mountain jersey | Men | Jean Alavoine | France | 1 |
| 2007 | Road Cycling | Vuelta a España | Mountain jersey | Men | Denis Menchov | Russia | 1 |
| 1985 | Road Cycling | Giro de Italia | Mountain jersey | Men | José Luis Navarro | Spain | 1 |
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