Roland Weißpflog participated in two Winter Olympics: in 1964 at Innsbruck with the mixed German team, and in 1968 at Grenoble with East Germany, finishing 16th and ninth respectively in the individual Nordic combined. In 1964 and 1966 he won the East German national title, and in 1967 was, and in 1963 had finished, third. His father Roland Sr., and his brother Falko competed as ski jumpers, but never qualified for the Olympic Games.
