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.
Tsitsipas broke back to 4-4 in the second set, but then Fritz broke his serve easily for 5-4 and closed out the match with an ace for a love hold.
“I thought my level today was very high. I think I played a very good match. Beating him here gives me a lot of confidence,” said Fritz, who hit 17 winners. “It has given me the reassurance I need to know I can play well on clay.”
Fritz looking for 1st clay title
Fritz has won five career titles, including two this year, but none on clay.
The 2022 Indian Wells champion next faces fifth-seeded Andrey Rublev, after the Russian beat German qualifier Jan-Lennard Struff 6-1, 7-6 (5).
Medvedev, who saved two match points when he beat Alexander Zverev on Thursday, was distracted by the crowd at the end of the first set and spoke to the umpire about it.
He broke back to 2-2 in the fourth game of the second set, but swiped his racket on the ground in frustration after losing the match. Medvedev was looking to reach his sixth straight final this year, having won four titles in 2023.
“I have huge respect for everything he’s done,” Rune said. “It was not easy to stop him but I’m happy I managed to do it.”
Rune, who staged a comeback to beat Djokovic and win the Paris Masters last November, is aiming for his first title of the year.
The 19-year-old Dane next plays Italian Jannik Sinner, who is 21.
The seventh-seeded Sinner eased past No. 16 Lorenzo Musetti 6-2, 6-2 in an all-Italian quarterfinal to reach his third straight semifinal at Masters level this season.
“I felt great today on the court. I’m hitting the ball in the right spots in the right moments,” Sinner said. “I tried to stay aggressive, which I’ve done.”
Sinner broke Musetti twice in the second set and converted his first match point with a strong first serve that Musetti returned long.
The 21-year-old Sinner lost to Medvedev in the Miami Masters final two weeks ago and was beaten by second-ranked Carlos Alcaraz in the semis at Indian Wells before that.
Alcaraz and record 11-time champion Rafael Nadal pulled out of the Monte Carlo tournament.
Nadal said Friday he will also miss the Barcelona Open, further limiting his clay-court preparations for the French Open.
The 22-time Grand Slam champion said he had not fully recovered from a left hip flexor injury sustained at the Australian Open.
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