In 1957 Hernán Medina won stage six of the Vuelta a Colombia before winning three stages the following year, in addition to finishing second overall in the race’s general classification. In the same year Medina had four podium finishes at stages of the Vuelta a Guatemala, also winning the overall classification. He continued to have success at the Vuelta a Colombia, winning three stages in 1959 and the overall classification in 1960. These performances earned Medina a place on the Olympic team, where he finished 28th in the individual road race at the Roma Games. One year after the Olympics he won another stage at the Vuelta a Colombia, in addition to finishing the race in second place.