In 1964 Damolin won the silver medal in the Nordic combined at the Italian championships and thus achieved his first success. Shortly afterwards he started at the Olympic Winter Games in Innsbruck in 1964 , where he finished 8th in the individual Nordic Combined. From 1965 to 1967 he won the Italian championship in combination. At the Four Hills Tournament 1966/67 he started for the first time in two competitions, but could not achieve a front placement. In 1968 he won gold in ski jumping and silver in combination at the Italian championships. At the 1968 Winter Olympics in Grenoble , he finished fifth in the combination and narrowly missed the medal ranks. In 1969 he was able to win the Italian championship title in combination again. In ski jumping he won the bronze medal behind Albino Bazzana and Mario Cecon . At the Nordic World Ski Championships in 1970 , he reached fifth place in the individual competition of the combination. In 1972 he again won gold in combination and bronze in ski jumping at the Italian championships. In 1974 he won gold again in ski jumping. At the 1972 Winter Olympics in Sapporo , he stepped in addition to the combination, in which he was 16th in the individual, for the first time in ski jumping. There he reached 55th place from the normal hill. In 1976 he won his last medal with silver at the Italian championships behind Francesco Giacomelli .