British number one Cameron Norrie was beaten by Albert Ramos-Vinolas in the Monte Carlo Masters second round.
Norrie forced a deciding set before Spain's Ramos-Vinolas, who was hampered by an abdominal injury, came through 6-4 2-6 6-4.
World number 37 Ramos-Vinolas has won all four of his matches on clay against the 10th-ranked Norrie.
Compatriot Dan Evans lost his second-round match 7-6 (7-3) 6-2 to Belgian David Goffin.
British number two Evans, who reached the semi-finals of the event last year, cut a frustrated figure in the closing stages of his match.
He saved seven of 10 break points, but was unable to make inroads on Goffin's serve.