Roland Weißpflog jr. started for SC Traktor Oberwiesenthal and weighed 75 kg at the competition times and was 1.78 m tall. His father Roland Weißpflog was a successful skier and his brother Falko a successful ski jumper and flyer. He took part in the Winter Olympics twice. At the Games in Innsbruck in 1964, only one individual competition was held in the Nordic Combined. Weißpflog reached sixteenth place out of 32 starters and was thus the third-best German of the all-German team, after the ski jumping he was still fourth. With ninth place, things went better for him in Grenoble in 1968 . There he competed for the GDR , which provided an independent team for the first time. He awarded a better place in jumping, which he finished in 29th place. With the second-best time on the trail behind the Swiss silver medalist Alois Kälin , Weißpflog still ran into the top ten and - by improving the average times in the run, which was the basis for the point scoring - helped the German Franz Keller to win the Olympic Games, his teammate Andreas Kunz was third. In 1963 Weißpflog was third in the GDR championships, GDR champion in 1964 and 1966 and runner-up in 1967.