American Taylor Fritz upset two-time defending champion Stefanos Tsitsipas 6-2, 6-4 to reach the Monte Carlo Masters semifinals on Friday.
The second-seeded Tsitsipas was followed out of the tournament by third-seeded Daniil Medvedev, who lost 6-3, 6-4 to sixth-seeded Holger Rune of Denmark.
It means the top three seeds have now been knocked out of the clay-court tournament following 22-time Grand Slam champion Novak Djokovic's exit in the third round on Thursday.
Tsitsipas was on a 12-match winning streak on the Cote d'Azur, where he claimed his two Masters 1,000 titles. "I stuck to the strategy of pulling the trigger and not letting him dictate with his forehand," the eighth-seeded Fritz said.
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