British number one Dan Evans was unable to earn a clay-court win before next week's French Open after losing to Greek second seed Stefanos Tsitsipas in the Hamburg Open first round.
Evans, ranked 34th, lost 6-3 6-1 as world number six Tsitsipas showed his quality in a 59-minute win.
Evans will head to Paris for the Grand Slam event which starts on Sunday.
Liam Broady is one more victory from joining him in the main draw after winning his second qualifying match.
British number six Broady won 7-6 (7-5) 7-6 (10-8) against Dutchman Botic van de Zandschulp at Roland Garros on Wednesday, surviving a set point in the opener and four more in the second set.
The 26-year-old has never played in the main draw and will earn his spot there if he can beat Australia's world number 122 Marc Polmans in the third and final qualifying round.
Fellow Briton Samantha Murray Sharan was also aiming to reach the main draw of the women's singles for the first time, but lost 6-3 7-6 (7-1) to Australia's Arina Rodionova in her opening qualifier.
Meanwhile, British men's number three Cameron Norrie suffered a shock defeat at a Challenger event in Italy.
Second seed Norrie, who is ranked 71st in the world, lost 6-2 6-4 to Italian world number 343 Andrea Pellegrino.