Cameron Norrie missed out on a semi-final spot at the Barcelona Open with defeat by Tomas Martin Etcheverry.
British number one Norrie, 31st in the world, sits just one place lower than Etcheverry in the ATP rankings.
There was little to separate the pair, but the Argentine stormed through the tie-breaks to win 7-6 (7-4) 7-6 (7-1).
British number two Jack Draper also fell at the quarter-final stage of the Bavarian International, losing to American third seed Taylor Fritz.
Fritz fought back from a set down to claim a 4-6 6-3 7-6 (7-1) victory and will face Chile’s Cristian Garin after the world number 106 knocked out German top seed Alexander Zverev with a 6-4 6-4 win.
Holger Rune of Denmark continued his bid for a third straight Bavarian International title by beating Switzerland’s Marc-Andrea Husler in straight sets.
Meanwhile in Barcelona, Norwegian third seed Casper Ruud, who claimed a straightforward 6-4 6-3 win over Italy’s Matteo Arnaldi, awaits Etcheverry.
On the other side of the draw, Greek Stefanos Tsitsipas survived a scare against Argentina’s Facundo Diaz Acosta.
In a thrilling encounter that lasted for two hours and 31 minutes, the fifth seed saved two match points before securing a 4-6, 6-3, 7-6 (10-8) triumph.
Tsitsipas, who won the Monte Carlo Masters earlier this month, will take on either French 16th seed Arthur Fils or Dusan Lajovic of Serbia in the semi-finals.