Defending champion Stefanos Tsitsipas and third seed Daniil Medvedev have been knocked out of the Monte Carlo Masters in the quarter-finals.
Tsitsipas, 24, lost the opening four games on his way to a 6-2 6-4 defeat by the American eighth seed Taylor Fritz.
Russian Medvedev, 27, was beaten in straight sets 6-3 6-4 by Dane Holger Rune, who is seeded sixth.
Italian Lorenzo Musetti takes on compatriot Jannik Sinner in the remaining last-eight tie on Friday.
Greek Tsitsipas, ranked third in the world, battled back in the second set against Fritz but was eliminated in just over an hour.