Ray Whiteside came from an athletic family, as his father, Eric Whiteside, competed for India in athletics at the 1936 Olympics. His athletic genes showed early as he excelled in athletics and boxing while in school at Sherwood College. After his family emigrated to Australia in 1948, he took up hockey and was selected to play for the Victorian Under-21 hockey team in 1951. He competed on the Victorian State team for the next six years, and was first capped in 1955 against New Zealand. His business career started in accounting, but he later entered sales with IBM, and was one of the pioneers in introducing personal computers to Australia.