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Oscar Chalupsky (born 1 March 1963) is a South African paddler. He was South Africa's team captain at the 1992 Summer Olympics in Barcelona where he competed in K-4 1000 m event, reaching the semi-finals. He is also a 12 time World Surfski Champion - his latest win (2012) coming at the age of 49, 29 years after his first win.

He attended Westville Boys' High School in Durban, South Africa. In 1979 he became the youngest ever South African to represent his country in life-saving. In his final year at school, 1980, he represented Natal at Craven Week Rugby, received South African colours for water polo and life-saving, and became the first person ever to win both the junior and senior men's Iron Man titles.

He founded Epic Kayaks and was Vice President until 2015 when he joined Nelo Kayaks as CEO. He is currently based in Portugal.