Winkler was born in Barmen, today part of Wuppertal, North Rhine-Westphalia, Germany, the son of a riding teacher.

Winkler won his first German championship in 1952, but could not participate in the Olympic Games in Helsinki that year because he was classified as a professional due to his teaching in the 1940s.

[3] In 1956 the Equestrian Games were held in Stockholm, as the athletes and their horses were not allowed to travel to Melbourne due to quarantine restrictions.

[5] In the first round Winkler pulled a groin muscle at the penultimate obstacle after his mare took off early and threw him out of position.

[3] Winkler worked as a trainer for the German Olympic teams, along with Paul Schockemöhle and Herbert Mayer, leading them to success in Seoul in 1988.

[2] He consulted companies who wanted to sponsor equestrian sport, organized tournaments, and worked for the development of young riders.

[8] He later published numerous books on riding and in 1991 founded the HGW-Marketinggesellschaft, a sports marketing firm that has helped produce various equestrian competitions.

[3][10] On 12 June 2008, he received the Federal Cross of Merit in Warendorf from Ingo Wolf [de], minister of interior and sport in North Rhine-Westphalia.