Born in Stuttgart, Winkelhock raced in junior formulae including Formula König, German Formula Renault, and the Formula Renault Eurocup between 1998 and 2000. He progressed to the German Formula 3 Championship in 2001, achieving three wins and fifth overall; one win and seventh in 2002; and two wins and fourth in 2003, when the series became the F3 Euroseries. In 2004, he competed in the DTM with an AMG-Mercedes CLK for the Persson team but failed to score any points. He returned to single-seater racing in 2005, joining the World Series by Renault with Draco, where he won three times but also crashed in qualifying and on the first lap at Monaco.
On 24 January 2006, Winkelhock was confirmed as test and reserve driver for the Midland F1 team (formerly Jordan Grand Prix) for the 2006 Formula One season, participating in Friday sessions at the Bahrain, Australian, German and Hungarian Grands Prix. He was re-signed for 2007 by the team, by then renamed Spyker F1, and also started three DTM races that year.
Following Christijan Albers's departure from Spyker after the 2007 British Grand Prix, Winkelhock was confirmed as his replacement for a single race—the 2007 European Grand Prix at the Nürburgring.
Winkelhock started last on the 22-car grid alongside team-mate Adrian Sutil. On the formation lap, with the rest of the field on dry-weather tyres, Spyker made a last-second decision to call him into the pits to fit full wet tyres. When heavy rain forced almost all other drivers to pit at the end of lap one, Winkelhock moved into the lead—passing Kimi Räikkönen on track as the Finn returned to the pits—and built a lead of 19 seconds by the end of lap two. By lap four, he led Felipe Massa by 33 seconds.
The stewards sent out the safety car and then suspended the race following a series of spins at the first corner. At the restart, Winkelhock and his team chose to remain on full wet tyres on a drying track, expecting further rain; the gamble failed and he quickly fell down the order before retiring on lap 15 with hydraulic problems that caused a small fire. He had led for a total of six laps. According to Bob Varsha of the Speed Channel commentary team, Winkelhock is the only driver in Formula One history to start last on the grid and lead a race on his Grand Prix debut, and also—because of the red flag and restart—the only driver to start both last and first on the grid in the same Grand Prix. Despite this performance, Spyker opted to give the remaining races to Super Aguri test driver Sakon Yamamoto.
After losing his Spyker seat, Winkelhock returned to the Deutsche Tourenwagen Masters with Team Rosberg, finishing 12th in 2008, 10th in 2009, and 12th again in 2010. In 2011, he competed in the FIA GT1 World Championship for All-Inkl.com Münnich Motorsport alongside Marc Basseng, driving a Lamborghini. The team switched to a Mercedes SLS due to a change in regulations and won the championship in 2012.
Winkelhock was set to join Münnich Motorsport in the World Touring Car Championship for 2013 but left before the season began to focus on GT racing; he was replaced by defending champion Robert Huff. From 2013, he competed primarily in the Blancpain Endurance Series and won the 2017 24 Hours of Nürburgring. In 2021, he made a brief DTM comeback with Abt Sportsline, replacing Sophia Flörsch for the Nürburgring round while she fulfilled Le Mans commitments.
This article is based solely on the supplied corpus. No external sources were consulted; claims that could not be substantiated against the corpus were omitted under the drop-the-claim rule.
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