Holder Stefanos Tsitsipas moved into the Monte Carlo Masters quarter-finals with a 7-5 7-6(1) victory over Laslo Djere on Thursday while fourth seed Casper Ruud was knocked out in straight sets by Grigor Dimitrov.
Tsitsipas broke only once in a match where break points were in short supply but the Greek third seed pounced when it mattered most at the end of both sets to seal victory.
The opening set went with serve but Djere was nearly broken when he was down 5-4 after he made three double faults. Djere held on but Tsitsipas switched gears and broke him in his next service game when the Serbian fired wide on set point.
The second set was nearly identical to the first with just one break point between the two. This time Djere forced a tiebreak, but Tsitsipas was unstoppable as he took the first five points before sealing the match with a forehand winner.
"I knew that I was going to have to be alert and 100%, he's someone that can compete very well on clay... I really had to work hard for this win," Tsitsipas said in an on-court interview.
Earlier, Norwegian Ruud became the tournament's latest high-profile casualty as he went down 6-3 7-5 to Bulgarian Dimitrov, who moved into the quarter-finals for a fourth time.
Unseeded Spaniard Alejandro Davidovich Fokina, who beat world number one Novak Djokovic earlier this week, reached the last eight with a 6-4 6-1 win over David Goffin.
He will meet 10th seed Taylor Fritz, who beat doubles partner Sebastian Korda 7-6(4) 7-5 in a battle of Americans.
"I fought off his returns on my second serves, which was the main focus. It was really good conditions today, so I was able to play what I felt was my best match," Fritz said.
Zverev through to Round of 16
World number three Alexander Zverev outclassed Federico Delbonis 6-1 7-5 in Monte Carlo on Wednesday to reach the last 16 of the Masters tournament after top seeds Carlos Alcaraz and Felix-Auger Aliassime crashed out.
Zverev, who took to court as the highest ranked player remaining in the tournament, lost the first four points of the match but breezed through the first set in just over 20 minutes and dropped only three points on serve.
The 24-year-old was tested by Delbonis in the second, fighting back from 2-4 down and winning the next 11 points to move within a game of victory before converting his third match point.
"It's not bad for a change of surface after Miami, you have to take that into consideration a little bit. I'm happy with the win," said Zverev, who lost to Norwegian Casper Ruud in the quarter-final of the hardcourt event.
The German's best run in the Principality tournament was 2018 when he reached the semi-finals, while he exited last year in the third round.
"I know that I have to play much better," Zverev added. "This is the only Masters on clay that I haven't won. I'm very motivated to do that and hope I can show it on court this week.
Earlier, unseeded American Sebastian Korda mastered the windy conditions to topple world number 11 Alcaraz 7-6(2) 6-7(5) 6-3 in an entertaining battle that lasted just over three hours, with both players struggling for rhythm.
"After losing to a Spaniard in Indian Wells and serving for it, it was nice to get a victory today," said the 21-year-old Korda, who pushed Rafa Nadal to a third-set tiebreak at the California tournament. "It was a crazy match!"
Korda will take on compatriot and Indian Wells winner Taylor Fritz after he beat former U.S. Open champion Marin Cilic 6-3 4-6 6-4 while Zverev will face Pablo Carreno Busta, who advanced after Alexander Bublik retired in the third set.
Miami Open champion Alcaraz followed top seed Novak Djokovic out of the tournament and was joined by Auger-Aliassime as the Canadian world number nine fell 6-2 7-6(2) to an inspired Lorenzo Mussett in front of a raucous crowd.
Last year's finalist Andrey Rublev prevailed 2-6 6-1 6-4 over Alex de Minaur, fourth seed Ruud saw off Holger Rune 7-6(5) 7-5 and Jannik Sinner got past Finnish qualifier Emil Ruusuvuori 7-5 6-3 in other second-round matches.