British number three Kyle Edmund lost to third seed Benoit Paire in the second round of the Estoril Open.
Despite winning the first set on a tie-break, the 21-year-old was beaten 6-7 (4-7) 6-3 6-3 by his French opponent.
Yorkshireman Edmund, who beat Spain's Daniel Gimeno-Traver in the previous round of the clay-court event, is ranked 89 in the world.
Paire, 26, who is 21st in the ATP rankings, will next face Spaniard Guillermo Garcia-Lopez.