Milton participated but did not win any medals at the 1988 Innsbruck Winter Paralympics. At the 1992 Tignes-Albertville Winter Paralympics, he won a gold medal in the Men's Slalom LW2 event, for which he received a Medal of the Order of Australia, and a silver medal in the Men's Super-G LW2 event. He became the first Australian to win a gold medal at a winter Olympics or Paralympics. That year he also won the slalom in the Austrian championships, and in 1993 he won both the slalom and super giant slalom at the Columbia Crest Cup. At the 1994 Lillehammer Winter Paralympics, he won a gold medal in the Men's Giant Slalom LW2 event, a silver medal in the Men's Slalom LW2 event, and two bronze medals in the Men's Downhill LW2 and Men's Super-G LW2 events. In January 1996, he won a gold, silver and bronze medal at the World Skiing Championships held in Austria.