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| Year | Sport | Contest | Discipline | Category | Name | Country | Position |
|---|---|---|---|---|---|---|---|
| 1996 | Road Cycling | Vuelta a España | Sprint jersey | Men | Laurent Jalabert | France | 1 |
| 1995 | Road Cycling | Vuelta a España | Sprint jersey | Men | Laurent Jalabert | France | 1 |
| 1994 | Road Cycling | Vuelta a España | Sprint jersey | Men | Laurent Jalabert | France | 1 |
| 1993 | Road Cycling | Vuelta a España | Sprint jersey | Men | Tony Rominger | Switzerland | 1 |
| 1992 | Road Cycling | Vuelta a España | Sprint jersey | Men | Djamolidine Abdoujaparov | Russia | 1 |
| 1991 | Road Cycling | Vuelta a España | Sprint jersey | Men | Uwe Raab | Germany | 1 |
| 1990 | Road Cycling | Vuelta a España | Sprint jersey | Men | Uwe Raab | East Germany | 1 |
| 1989 | Road Cycling | Vuelta a España | Sprint jersey | Men | Malcolm Elliott | Great Britain | 1 |
| 1988 | Road Cycling | Vuelta a España | Sprint jersey | Men | Sean Kelly | Ireland | 1 |
| 1987 | Road Cycling | Vuelta a España | Sprint jersey | Men | Alfonso Gutiérrez | Spain | 1 |
| 1986 | Road Cycling | Vuelta a España | Sprint jersey | Men | Sean Kelly | Ireland | 1 |
| 1985 | Road Cycling | Vuelta a España | Sprint jersey | Men | Sean Kelly | Ireland | 1 |
| 1984 | Road Cycling | Vuelta a España | Sprint jersey | Men | Guido Van Calster | Belgium | 1 |
| 1983 | Road Cycling | Vuelta a España | Sprint jersey | Men | Marino Lejarreta | Spain | 1 |
| 1982 | Road Cycling | Vuelta a España | Sprint jersey | Men | Stefan Mutter | Switzerland | 1 |
| 1981 | Road Cycling | Vuelta a España | Sprint jersey | Men | Francisco Javier Cedena | Spain | 1 |
| 1980 | Road Cycling | Vuelta a España | Sprint jersey | Men | Sean Kelly | Ireland | 1 |
| 1979 | Road Cycling | Vuelta a España | Sprint jersey | Men | Fons De Wolf | Belgium | 1 |
| 1978 | Road Cycling | Vuelta a España | Sprint jersey | Men | Ferdi Van den Haute | Belgium | 1 |
| 1977 | Road Cycling | Vuelta a España | Sprint jersey | Men | Freddy Maertens | Belgium | 1 |
| 1976 | Road Cycling | Vuelta a España | Sprint jersey | Men | Dietrich Thurau | West Germany | 1 |
| 1975 | Road Cycling | Vuelta a España | Sprint jersey | Men | Miguel María Lasa | Spain | 1 |
| 1974 | Road Cycling | Vuelta a España | Sprint jersey | Men | Domingo Perurena | Spain | 1 |
| 1973 | Road Cycling | Vuelta a España | Sprint jersey | Men | Eddy Merckx | Belgium | 1 |
| 1972 | Road Cycling | Vuelta a España | Sprint jersey | Men | Domingo Perurena | Spain | 1 |
| 1971 | Road Cycling | Vuelta a España | Sprint jersey | Men | Cyrille Guimard | France | 1 |
| 1970 | Road Cycling | Vuelta a España | Sprint jersey | Men | Guido Reybrouck | Belgium | 1 |
| 1969 | Road Cycling | Vuelta a España | Sprint jersey | Men | Raymond Steegmans | Belgium | 1 |
| 1968 | Road Cycling | Vuelta a España | Sprint jersey | Men | Jan Janssen | Netherlands | 1 |
| 1967 | Road Cycling | Vuelta a España | Sprint jersey | Men | Jan Janssen | Netherlands | 1 |
| 1966 | Road Cycling | Vuelta a España | Sprint jersey | Men | Jos van der Vleuten | Netherlands | 1 |
| 1965 | Road Cycling | Vuelta a España | Sprint jersey | Men | Rik Van Looy | Belgium | 1 |
| 1964 | Road Cycling | Vuelta a España | Sprint jersey | Men | José Perez-Frances | Spain | 1 |
| 1963 | Road Cycling | Vuelta a España | Sprint jersey | Men | Bas Maliepaard | Netherlands | 1 |
| 1962 | Road Cycling | Vuelta a España | Sprint jersey | Men | Rudi Altig | West Germany | 1 |
| 1961 | Road Cycling | Vuelta a España | Sprint jersey | Men | Antonio Suárez | Spain | 1 |
| 1960 | Road Cycling | Vuelta a España | Sprint jersey | Men | Arthur De Cabooter | Belgium | 1 |
| 1959 | Road Cycling | Vuelta a España | Sprint jersey | Men | Rik Van Looy | Belgium | 1 |
| 1958 | Road Cycling | Vuelta a España | Sprint jersey | Men | Salvador Botella | Spain | 1 |
| 1957 | Road Cycling | Vuelta a España | Sprint jersey | Men | Vicente Iturat | Spain | 1 |
| 1956 | Road Cycling | Vuelta a España | Sprint jersey | Men | Rik Van Steenbergen | Belgium | 1 |
| 1955 | Road Cycling | Vuelta a España | Sprint jersey | Men | Fiorenzo Magni | Italy | 1 |
| 1947 | Road Cycling | Vuelta a España | Sprint jersey | Men | Delio Rodríguez | Spain | 1 |
| 1945 | Road Cycling | Vuelta a España | Sprint jersey | Men | Delio Rodríguez | Spain | 1 |
| 2025 | Road Cycling | Vuelta a España | Mountain jersey | Men | Jay Vine | Australia | 1 |
| 2024 | Road Cycling | Vuelta a España | Mountain jersey | Men | Jay Vine | Australia | 1 |
| 2023 | Road Cycling | Vuelta a España | Mountain jersey | Men | Remco Evenepoel | Belgium | 1 |
| 2022 | Road Cycling | Vuelta a España | Mountain jersey | Men | Richard Carapaz | Ecuador | 1 |
| 2021 | Road Cycling | Vuelta a España | Mountain jersey | Men | Michael Storer | Australia | 1 |
| 2020 | Road Cycling | Vuelta a España | Mountain jersey | Men | Guillaume Martin | France | 1 |
| 2019 | Road Cycling | Vuelta a España | Mountain jersey | Men | Geoffrey Bouchard | France | 1 |
| 2018 | Road Cycling | Vuelta a España | Mountain jersey | Men | Thomas De Gendt | Belgium | 1 |
| 2017 | Road Cycling | Vuelta a España | Mountain jersey | Men | Davide Villella | Italy | 1 |
| 2016 | Road Cycling | Vuelta a España | Mountain jersey | Men | Omar Fraile | Spain | 1 |
| 2015 | Road Cycling | Vuelta a España | Mountain jersey | Men | Omar Fraile | Spain | 1 |
| 2014 | Road Cycling | Vuelta a España | Mountain jersey | Men | Luis León Sánchez | Spain | 1 |
| 2013 | Road Cycling | Vuelta a España | Mountain jersey | Men | Nicolas Edet | France | 1 |
| 2012 | Road Cycling | Vuelta a España | Mountain jersey | Men | Simon Clarke | Australia | 1 |
| 2011 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 2010 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 2009 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 2008 | Road Cycling | Vuelta a España | Mountain jersey | Men | David Moncoutié | France | 1 |
| 2007 | Road Cycling | Vuelta a España | Mountain jersey | Men | Denis Menchov | Russia | 1 |
| 2006 | Road Cycling | Vuelta a España | Mountain jersey | Men | Egoi Martínez | Spain | 1 |
| 2005 | Road Cycling | Vuelta a España | Mountain jersey | Men | Joaquim Rodríguez | Spain | 1 |
| 2004 | Road Cycling | Vuelta a España | Mountain jersey | Men | Félix Cárdenas | Colombia | 1 |
| 2003 | Road Cycling | Vuelta a España | Mountain jersey | Men | Félix Cárdenas | Colombia | 1 |
| 2002 | Road Cycling | Vuelta a España | Mountain jersey | Men | Aitor Osa | Spain | 1 |
| 2001 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 2000 | Road Cycling | Vuelta a España | Mountain jersey | Men | Carlos Sastre | Spain | 1 |
| 1999 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 1998 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 1997 | Road Cycling | Vuelta a España | Mountain jersey | Men | José María Jiménez | Spain | 1 |
| 1996 | Road Cycling | Vuelta a España | Mountain jersey | Men | Tony Rominger | Switzerland | 1 |
| 1995 | Road Cycling | Vuelta a España | Mountain jersey | Men | Laurent Jalabert | France | 1 |
| 1994 | Road Cycling | Vuelta a España | Mountain jersey | Men | Luc Leblanc | France | 1 |
| 1993 | Road Cycling | Vuelta a España | Mountain jersey | Men | Tony Rominger | Switzerland | 1 |
| 1992 | Road Cycling | Vuelta a España | Mountain jersey | Men | Carlos Hernández | Spain | 1 |
| 1991 | Road Cycling | Vuelta a España | Mountain jersey | Men | Lucho Herrera | Colombia | 1 |
| 1990 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Martín Farfán | Colombia | 1 |
| 1989 | Road Cycling | Vuelta a España | Mountain jersey | Men | Óscar Vargas | Colombia | 1 |
| 1988 | Road Cycling | Vuelta a España | Mountain jersey | Men | Álvaro Pino | Spain | 1 |
| 1987 | Road Cycling | Vuelta a España | Mountain jersey | Men | Lucho Herrera | Colombia | 1 |
| 1986 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1985 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1984 | Road Cycling | Vuelta a España | Mountain jersey | Men | Felipe Yáñez | Spain | 1 |
| 1983 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1982 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1981 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Laguía | Spain | 1 |
| 1980 | Road Cycling | Vuelta a España | Mountain jersey | Men | Juan Fernández | Spain | 1 |
| 1979 | Road Cycling | Vuelta a España | Mountain jersey | Men | Felipe Yáñez | Spain | 1 |
| 1978 | Road Cycling | Vuelta a España | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1977 | Road Cycling | Vuelta a España | Mountain jersey | Men | Pedro Torres | Spain | 1 |
| 1976 | Road Cycling | Vuelta a España | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1975 | Road Cycling | Vuelta a España | Mountain jersey | Men | Andrés Oliva | Spain | 1 |
| 1974 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Abilleira | Spain | 1 |
| 1973 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Luis Abilleira | Spain | 1 |
| 1972 | Road Cycling | Vuelta a España | Mountain jersey | Men | José Manuel Fuente | Spain | 1 |
| 1971 | Road Cycling | Vuelta a España | Mountain jersey | Men | Joop Zoetemelk | Netherlands | 1 |
| 1970 | Road Cycling | Vuelta a España | Mountain jersey | Men | Agustín Tamames | Spain | 1 |
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