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Taking his record to 3-0 against the top seed, the Argentine ended Zverev's seven-match winning streak, which dated back to the start of his Munich title run.

In a rematch of their fourth-round encounter from 12 months ago, Cerundolo repeated the result with another straight-sets win. The 20th seed, who also beat Zverev this season in Buenos Aires, saved the only break point he faced.

"I'm super happy because I know he loves playing here. He told me last year when I beat him," Cerundolo said. "He's an incredible player. I have a great relationship with him, so super happy to get another win and to be in the quarter-finals again."

With the win, Cerundolo joined Arthur Fils as the only players to reach three ATP Masters 1000 quarter-finals this season. He also leads the ATP Tour with seven quarter-finals and 15 clay-court wins on the 2025 season.

"This year I learned to play bad and win matches. I gained the capacity to win playing not my best tennis," Cerundolo said. "I'm super happy with what I'm doing during this year."

All five of Cerundolo's victories against Top five opponents in the ATP rankings have come on clay: three against Zverev and two against Casper Ruud. Up two places to No. 19 in the ATP Live rankings — a mark that would match his career-high — Cerundolo will next face Miami champion Jakub Mensik. 

The 19 year-old Czech could pass him in the live rankings with a win, while Cerundolo could move to No. 18 with a victory.

While Cerundolo is through to his seventh career Masters 1000 quarter-final, Zverev was denied his 100th quarter-final appearance at that prestigious level.

Ninth seed Daniil Medvedev avoided an upset of his own to match his career-best Madrid result. The 29 year-old advanced to the last eight by rallying past 31st-seeded American Brandon Nakashima 3-6, 6-1, 6-4, closing the one-hour, 49-minute encounter on his fifth match point.

“The ball was bouncing so high, it was so tough to control,” Medvedev said, discussing the conditions. “I feel like for both of us, because we both made a lot of unforced errors. 

"I got pretty angry at the end of the first set because I couldn’t control what I was doing on the court, but I felt like I’m not far from winning games and then winning the match, so I knew that I just had to stay tougher, play just a tiny bit better and I managed to do it.”

Medvedev will next face third seed 14th seed Casper Ruud. Should Medvedev win, he will become the fifth man to complete the set of semi-finals at all active ATP Masters 1000 events, alongside Novak Djokovic, Roger Federer, Rafael Nadal and Andy Murray.

Medvedev, number-nine in the ATP live rankings with Lorenzo Musetti just 40 points behind, is seeking his first title since winning Rome in 2023.

Ruud defeated Taylor Fritz 7-5, 6-4 to reach his first ATP Masters 1000 quarter-final since Monte-Carlo last year and 13th overall.

The 26 year-old survived a topsy-turvy first set, which he served for at 5-4 and held set point before Fritz broke. Ruud then opened a 0/40 lead the next game and eventually earned a break of his own. He capitalised on his second opportunity to serve out the set.

The Norwegian used his backhand down the line to great effect and drew errors from Fritz’s forehand. Fritz finished with 28 unforced errors, including 19 from his forehand. Ruud improved to 18-6 on the season and 17-0 after winning the first set.

Ruud's quarter-final clash with Medvedev will mark their fourth meeting and first since the 2021 ATP finals. While Medvedev leads their series 3-0, Ruud is 6-0 in ATP Masters 1000 clay-court quarter-finals.