Winkelhock driving in the German F3 series in 2002.
Born in Stuttgart, Winkelhock won races in a string of junior formulae including Formula König, German Formula Renault and the Formula Renault Eurocup from 1998–2000.
In 2001, Winkelhock joined the German Formula 3 Championship, where he remained until the championship became the F3 Euroseries in 2003. His record was fifth overall in 2001 (three wins), seventh in 2002 (one win) and fourth in 2003 (two wins).
He switched to touring car racing in 2004, with a season in the DTM in an AMG-Mercedes CLK. But he failed to score a point all year with the Persson team.
Winkelhock switched back to single-seater racing in 2005, joining the World Series by Renault with Draco. He won three times but there were also some less than shining moments – notably when he crashed at Monaco in qualifying and on the first lap of the race.