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No. 4 seed Casper Ruud of Norway, No. 5 seed Jack Draper of Great Britain and No. 7 seed Andrey Rublev of Russia were shown the exit door Thursday in the Round of 16 of the Rolex Monte-Carlo Masters in Monaco.

Australian Alexei Popyrin saved two match points on his way to a 6-4, 3-6, 7-5 upset of Ruud in nearly two hours and 58 minutes.

Ruud had opportunities to wrap up the match in the 10th game of the third set. Twice, Popyrin staved off defeat and won the game, the second of four games won in a row to rally to victory.

Spaniard Alejandro Davidovich Fokina pulled out a 6-3, 6-7 (6), 6-4 victory over Draper, overcoming 57 unforced errors by winning 18 of 23 points at the net and breaking Draper’s serve six times in 13 chances.

“Today I didn’t feel like I played my best tennis or gave my best mental strategy,” Davidovich Fokina said despite the win. “Today was a rollercoaster with my mind.”

French No. 12 seed Arthur Fils didn’t need three sets to earn his upset victory, as he swept past Rublev 6-2, 6-3.

Fils won 30 of 42 service points (71.4 percent) while ensuring that Rublev won less than half of his (25 of 53, 47.2 percent). Fils went 5-for-9 in converting break points against Rublev.

“From A to Z, I was very focused,” Fils said in French at his press conference. “I made the right choices. I was implementing my tactics. I was feeling good. This was a really good match.”

No. 2 seed Carlos Alcaraz of Spain is the only top-five seed still standing in the quarterfinals after his 6-3, 6-1 win over German qualifier Daniel Altmaier in the Round of 16. Alcaraz faced 10 break points but saved nine.

“The score doesn’t show how difficult it was,” Alcaraz said. “… I had to battle in the first set.”

This is Alcaraz’s first time into the quarterfinals of the Monte-Carlo Masters, and he could be in line for his sixth career ATP Masters 1000 title this week. His next opponent will be Fils, while Popyrin will meet Davidovich Fokina.

No. 6 seed Stefanos Tsitsipas of Greece dominated Portugal’s Nuno Borges 6-1, 6-1 in 67 minutes and advanced to face 13th seed Lorenzo Musetti, a 6-3, 6-3 winner over fellow Italian Matteo Berrettini.

Australian eighth seed Alex de Minaur topped ninth seed Daniil Medvedev of Russia 6-2, 6-2. His quarterfinal foe will be No. 15 seed Grigor Dimitrov of Bulgaria, who defeated Chile’s Alejandro Tabilo 6-3, 3-6, 6-2.

–Field Level Media