Daniil Medvedev survived a dramatic late-night marathon against Alexander Zverev on Thursday at the Rolex Monte-Carlo Masters, where the third seed rallied to a 3-6, 7-5, 7-6(7) third-round victory.

Zverev served for the match at 5-4 in both the second and third sets and let slip two match points in the deciding-set tie-break on Court Rainier III, but he was unable to see off the ever-persistent Medvedev. A closely fought contest, during which both men produced high-quality play but struggled to do so consistently, was ultimately decided when Medvedev remained the more solid in the closing moments.

Medvedev trailed 5/6 and 6/7 in the deciding-set tie-break but Zverev errors on both points cost the German dear. Medvedev reeled off three points in a row to complete the win and reach the Monte-Carlo quarter-finals for the second time.

“That was a crazy match,” said Medvedev. “He served two times for the match, he probably should have done better, but that is also clay courts. I tried to watch a lot of tennis before playing this tournament, and one thing that I saw is you can come back at any moment. The serve doesn’t count as much, so as soon as someone gets a little bit tight, the match can turn around in one second. That’s what I managed to do.”

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Both players enjoyed plenty of success on return in a topsy-turvy third-round encounter. Zverev broke Medvedev’s serve six times, but the World No. 5 converted six of 13 of his own break points en route to a three-hour, five-minute victory that increased his ATP Head2Head series lead against the German to 8-6.

Medvedev is now 31-3 for the season, having won 26 of his past 27 tour-level matches. The 27-year-old is chasing his maiden title on clay this week in Monte-Carlo, and Thursday’s win against Zverev represents his first win against a Top 20 opponent on the surface since he beat Kei Nishikori in Barcelona in 2019.

His opponent in the last eight will be Holger Rune. The 19-year-old Dane advanced to his maiden Monte-Carlo quarter-final after Matteo Berrettini, was forced to withdraw from the pair’s third-round clash due to an oblique injury. It will be a first ATP Head2Head clash between Medvedev and Rune, although the pair is not completely unfamiliar with each others games.

“He’s an amazing player,” said Medvedev of Rune. “We practised many times. The first time at the Nitto ATP Finals when he was still a junior. Then a lot of times at the Mouratoglou Academy. We practised a lot on clay. I don’t think I ever won a set, but I was playing good today, so I hope to show this good tennis tomorrow.”