Following the death of his brother Sidney in the Kyeema aircraft crash in 1938, Hill-Smith returned to South Australia to take on the management of the family winery, Yalumba at Angaston.[5] He led the company from 1938 to 1986.[6] In 1980, Hill-Smith was appointed an Officer of the Order of the British Empire (OBE) for services to the wine industry and horse racing.[7]
A grandstand at Cheltenham Park Racecourse was named the Wyndham Hill Smith Grandstand.[8] His Wisden obituary concluded with the comment, "In later life he became famous for the liberal hospitality which he extended to touring teams at his Yalumba vineyard in South Australia."[9]