Winkler was one of Ulrich Wehling's training partners and one of the few who was able to beat him in an important competition ( 1978 World Cup in Lahti ). Winkler achieved his first international success at the Nordic Junior Ski World Championships in Autrans in 1974 , where he won the gold medal in the individual competition. A year later he won the individual silver medal in Lieto, Finland . At the 1976 Winter Olympics in Innsbruck he won the individual over 15 km and the bronze medal on the normal hill. He repeated this success at the 1980 Winter Olympics in Lake Placid . Previously, he was able to achieve his greatest success by winning the gold medal in the individual at the Nordic World Ski Championships in 1978 in Lahti . He finished the Holmenkollen Ski Festival in Oslo in 1981 and 1982 in singles in 2nd place and won it in the relay in 1982. At the 1982 World Championships in Oslo he won silver again behind Tom Sandberg and the gold medal in the 3 × 5 km relay, which was held for the first time.
In 1990 Konrad Winkler was appointed national coach for the Nordic combined, but was replaced in 1992 after disagreements with the Nordic combined and then worked as a junior coach. He later worked in Saalfelden ( Austria ). Winkler is currently working as a trainer at the Federal Police Sports School in Bad Endorf .