Australian Marinko Matosevic has been bundled out of the BMW Open in Munich after a tight second-round loss.
The 28-year-old was beaten in a close contest with Russian Dmitry Tursunov, going down 6-7 (6/8) 6-3 7-5.
Tursunov will now face qualifier Martin Klizan, who upset third seed Mikhail Youzhny.
Klizan, who has slumped to 111th in the rankings from a high of 26 last year, won a deciding tie-break to beat 2010 champion Youzhny 6-7 (5/7) 6-2 7-6 (7/2).
Meanwhile, qualifier Jan-Lennard Struff reached the quarter-finals with a 6-3 6-3 win over Sergiy Stakhovsky but he will have to wait to find out his opponent after Ricardas Berankis and Jurgen Melzer were forced off by darkness in the third set.
In the doubles, Ross Hutchins reached his first ATP Tour semi-final since his return from cancer.
The Londoner and Scottish partner Colin Fleming defeated second seeds Juan Sebastian Cabal and Robert Farah 6-1 6-4.