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.”

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.”

How would you do trying to guess the autographs of the best players on the ATP Tour?

Andrey Rublev, Alexander Zverev, Hubert Hurkacz, Alejandro Davidovich Fokina and Thanasi Kokkinakis gave it their best shot in the newest edition of the ATP Head-To-Head Challenge.

“This is not even a signature, No. 3,” Rublev said, cracking a laugh. “When the pen is not working, you try to make it [until], ‘Okay now it’s working’.”

“Is this person very good?” Kokkinakis asked about one autograph’s owner. “Is it Alcaraz? That’s not Zverev? Medvedev? Tsitsipas? Sinner? Is that Novak’s?”

One of the funniest moments of the feature came when Rublev made his guess for one of the autographs only to be told he was incorrect. After the 25-year-old made several more guesses, he was adamant that the signature belonged to the first player he guessed.

Who was wrong, Rublev or the producers? Take a look at the full feature to watch us roll back the tape.

Lloyd Glasspool and Harri Heliovaara reached a fourth consecutive ATP Masters 1000 quarter-final on Thursday, but the sixth-seeded pair did not have things all their own way at the Rolex Monte-Carlo Masters.

The British-Finnish team edged Argentine duo Maximo Gonzalez and Andres Molteni 5-7, 6-4, 10-8 in the Principality. Glasspool and Heliovaara, who are making their debut appearance at the first clay-court Masters 1000 event of the season, saved seven of nine break points they faced en route to a narrow one-hour, 46-minute second-round triumph.

Glasspool and Heliovaara reached the quarter-finals in both Indian Wells and Miami last month, runs that built on their charge to the semi-finals at last November’s Rolex Paris Masters. Their next opponents in Monte-Carlo will be Romain Arneodo and Sam Weissborn, who produced a major upset on Thursday by beating defending champions and second seeds Rajeev Ram and Joe Salisbury 6-2, 6-3.

The quarter-final lineup in Monte-Carlo was completed by fifth seeds Ivan Dodig and Austin Krajicek, who defeated Juan Sebastian Cabal and Robert Farah 7-6(4), 6-4.

Novak Djokovic suffered a stunning three-set defeat to Lorenzo Musetti on Thursday at the Rolex Monte-Carlo Masters. It is a match the World No. 1 wants to move on from quickly.

“I don’t think it’s catastrophic, but my feeling is bad right now because I lost the match,” Djokovic said. “That’s all. Congrats to my opponent. I move on.”

Djokovic arrived in Monte-Carlo with jaw-dropping serving statistics, averaging one service game lost per match played in 2023. But against Musetti, whom he had defeated in all three of their previous ATP Head2Head matches, the top seed lost his serve eight times.

“Well, [my] feeling is terrible after playing like this, honestly,” Djokovic said. “But congrats to him. He stayed tough in important moments, and that’s it. That’s all I can say. Good luck to him.”

Reporters at Djokovic’s press conference pressed the Serbian to learn if he thought a performance like this was coming.

“You always hope for the good day in the office,” Djokovic said. “But yeah, I know I’m not playing so great and he’s playing very well, so I knew it was going to be a tough match. “

This was his first tournament since Dubai in early March. Djokovic confirmed he will play next week at the Srpska Open in Banja Luka.

Lorenzo Musetti earned the biggest win of his career Thursday at the Rolex Monte-Carlo Masters, where he upset World No. 1 Novak Djokovic 4-6, 7-5, 6-4 to reach his second ATP Masters 1000 quarter-final.

Competing in wet and windy conditions on Court Rainier III, the 21-year-old Italian exploited a weak serving performance from Djokovic, breaking the Serbian eight times en route to a two-hour, 54-minute win. After converting his fourth match point, an emotional Musetti looked at his team and shook his head in disbelief.

“I am struggling not to cry,” Musetti said in his on-court interview. “It is an emotional win because it was a really long match. Three-hour match and suspended by rain. It was not easy conditions because it was a little bit windy and cold. Not like we used to play in the recent days. I am really proud of myself and I can see on the screen. I am struggling not to cry because it is a dream for me.”

After dropping the opening set, Musetti rallied from 2-4 in the second set to level. He hit with aggression and depth to force Djokovic into 11 unforced errors in the set and then continued to play with intensity and flair after a 59-minute rain delay at the start of the decider to earn the second Top 5 win of his career.

“I couldn’t find the right balance on [serve]. Particularly with the toss. I think we were returning better than serving,” Musetti said. “The rallies at the end were really intense and really long and it was a tough battle. Even for the physical and mental part. Beating Novak is something remarkable for me.”

With his ninth tour-level win of the season, Musetti improved to 1-3 in his ATP Head2Head series against Djokovic. He will next play countryman Jannik Sinner after the 21-year-old defeated Hubert Hurkacz earlier Thursday.

Djokovic began the week with an ATP Tour-leading 58.7 winning percentage behind his second serve according to Infosys ATP Stats. Against Musetti he won just 39 per cent of his second-serve points (12/31). Entering the match the Serbian had lost serve just 17 times in 17 matches this year. Against Musetti he dropped serve eight times. 

Musetti entered the clash with momentum, having defeated Miomir Kecmanovic 7-6(1), 6-0 and Luca Nardi 6-0, 6-0. The 21-year-old Italian, who is into his second Masters 1000 quarter-final after reaching the last eight in Paris in 2022, opened his shoulders as the match went on, crushing the ball off both wings to triumph.

“I am just going to enjoy this win for at least half an hour and then I will rest, recover and be ready for the next battle with a friend and fellow Italian,” Musetti added.

The 21-year-old is up to No. 20 in the Pepperstone ATP Live Rankings and would climb to No. 17 if he defeats Sinner. That would mark a new career-high for the Italian.

Djokovic was chasing a record-extending 39th ATP Masters 1000 title this week. The Serbian is a two-time champion in Monte-Carlo, having triumphed in 2013 and 2015.

Stefanos Tsitsipas is showing little sign of slowing down at the Rolex Monte-Carlo Masters.

The 2021 and 2022 champion extended his winning streak at the clay-court ATP Masters 1000 event to 12 matches on Thursday with a 6-3, 6-4 third-round victory against Nicolas Jarry.

The second-seeded Tsitsipas delivered a rock-solid display to seal a 93-minute victory against the World No. 58 Jarry on Court Rainier III. A single break of the Chilean’s serve in each set was enough to secure a quarter-final spot for Tsitsipas, who won 80 per cent (32/40) of points behind his own first delivery and saved both break points he faced.

“I had to deal with a few [tough] points, especially when he had break points,” reflected Tsitsipas. “I dealt with those situations very maturely and played precisely, so it was great out there.”

Although Tsitsipas carried a stellar Monte-Carlo record into his clash with Jarry, it was the Chilean who had triumphed in the pair’s only previous ATP Head2Head meeting on the grass of ‘s-Hertogenbosch in 2019. The Greek was pleased with the way he took control of a hard-fought encounter to ensure there would be no repeat of that result.

“He’s someone that has had good results on clay, someone that can serve big as well,” added Tsitsipas of Jarry, who lifted his second ATP Tour title at home in Santiago in February. “It was all sort of played in the small details, and I’m really happy that I pulled through and gave myself such a good ending to this match.”

Now the owner of a 14-2 record in Monte-Carlo, Tsitsipas next prepares for a quarter-final clash against eighth seed Taylor Fritz or Jiri Lehecka.