Defending champ upset in Munich
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The seventh-seeded Russian, who also won the tournament in 2004, dropped serve four times.
Sixth-seeded Mikhail Youzhny of Russia, the 2010 champion, edged out Philipp Petzschner of Germany 7-5, 7-5, and eighth-seeded Marcos Baghdatis of Cyprus outlasted Tobias Kamke of Germany 6-1, 3-6, 6-3 for his first clay-court win of the season.
Baghdatis broke serve four times and saved six of eight break points to advance in a tournament where he has twice been a semifinalist.
Copyright 2012 by The Associated Press