Naomi Broady lost 3-6 7-5 6-3 to France's Pauline Parmentier in their qualifying round match at the Luxembourg Open.
The British number three, who is ranked 132 in the world, made a strong start and produced eight aces but was unable to maintain her challenge with her service proving vulnerable in the decisive third set.
Parmentier now enters the first round of the hard court tournament in Luxembourg.
Fourth seed Sorana Cirstea retired from her first-round match.
After reaching the quarter-finals in Linz last week, the Romanian was unable to complete her contest with Veronica Cepede Royg, withdrawing midway through the second set.
Eighth seed Varvara Lepchenko also fell at the first hurdle.
Carrina Witthoeft sent her crashing out with a 7-6 (7/1) 2-6 7-6 (7/1) victory, despite the American smashing 10 aces.
The remaining seeds in action, Annett Kontaveit (third), Elise Mertens (fifth) and Beatriz Hadad Maja (seventh) did not drop a set between them in seeing off their respective obstacles Jana Cepelova, Sara Tormo and Kirsten Flipkens.
Madison Brengle also defeated Lara Arruabarrena 6-2 6-2.
Alize Cornet booked her place in the second round of the Kremlin Cup at the expense of local favourite Ekaterina Makarova.
Moscow-born Makarova never managed to get a foothold in the game, breaking three times but surrendering her own serve on twice as many occasions in a 6-3 6-3 loss.
Czech player Katerina Siniakova had earlier lit up Centre Court with a 6-0 6-2 victory over Donna Vekic.
The first set occupied barely 20 minutes and, though Vekic managed to get something on the board, it was a comprehensive thrashing.
Yulia Putintseva, from Kazakhstan, also scored a straight sets win over Olesya Purvushina 7-5 6-1.
Aliaksandra Sasnovich was made to work harder, coming from behind and working for two hours and 11 minutes to beat Timea Babos 1-6 7-6 6-4 (7/3).
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