From 2004 Winkler started in the Nordic Combined. In 2004 he became German student champion and won the OPA games . A year later he was two-time German youth champion and German vice-youth champion in special jumping. In September 2005 Winkler took fifth place in the Alpine Cup in Winterberg.
In September 2006 he switched from Nordic combined to ski jumping. He started in the FIS races , FIS Cup Juniors , Alpine Cup, Germany Cup and Continental Cup , among others . In 2009 and 2011 he won the overall standings in the German Cup. He achieved his best international result to date on July 30, 2011 at the Continental Cup in Courchevel, France , finishing fifth. He started for the first time at the Summer Grand Prix 2011 in Almaty and in Klingenthal , finished 18th and 16th and 54th overall. On December 30th 2011 Winkler made his World Cup debut at the start of the Four Hills Tournament in Oberstdorf . At the second stop for the New Year's event in Garmisch-Partenkirchen , he did not qualify. After two stops, he finished the Four Hills Tournament overall ranking in 65th place.
Germany