Konrad Winkler was one of the training partners of the famous Nordic combined athlete Ulrich Wehling and was the only one to beat him in a major international, this occurring at the 1978 World Championships where Winkler won gold. At the 1976 and 1980 Winter Olympics Winkler won the bronze medal behind Wehling. In his last year of competition he won a team gold and individual silver at the 1982 World Championship. After German reunification Winkler was the first East German to become a Nordic combined trainer in Germany. Nevertheless he had difficulties with his athletes and switched to the National Youth Team after the 1992 Winter Olympics. He later worked at Saalfelden, Austria and eventually at the National Police School at Bad Endorf, Germany.