Nikolay Davydenko followed up his Wimbledon first-round exit to Andy Murray by losing in the Mercedes Cup in Stuttgart.
Davydenko failed to take a match point as he lost in three sets to German wild card Dustin Brown in the first round.
The Russian veteran served for the match at 5-4 in the third set but missed his chance and Brown came through to win 7-5 3-6 7-6 (9-7) in two hours and four minutes.
Also in the first round, Belgium's Steve Darcis overcame Albert Montanes of Spain 6-2 6-4.
In an all-Spanish affair, Guillermo Garcia-Lopez beat Ruben Ramirez Hidalgo 6-2 6-3.
