Canada's Milos Raonic dropped a 7-5, 6-4 decision to Argentina's Carlos Berlocq in quarter-final play Friday at the Portugal Open.
Berlocq, the world No. 62, broke Raonic's serve on four occasions and limited the ninth-ranked Canadian to just six aces. The Argentine will meet Spanish qualifier Daniel Gimeno-Traver in the semifinals.
Gimeno-Traver advanced with a 6-1, 6-2 victory over Spain's Marcel Granollers.
Raonic, from Thornhill, Ont., has lost all four of his quarter-final appearances this season.
He will continue his preparation for the French Open next week at the Masters 1000 event in Madrid.
On Thursday, Montreal's Eugenie Bouchard lost her quarter-final matchup against Russia's Svetlana Kuznetsova.