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.

The last 16 is set at the Rolex Monte-Carlo Masters, with all eight third-round matches on the Thursday schedule in Monaco. An abundance of marquee matchups highlights the Day 5 action, led by the evening showdown between Daniil Medvedev and Alexander Zverev.

In addition to that rematch of the epic Indian Wells quarter-final won by Medvedev, Novak Djokovic will take on Lorenzo Musetti and two pairs of Top 10 seeds will square off as Jannik Sinner meets Hubert Hurkacz and Andrey Rublev plays Karen Khachanov. 

Other Top 10 seeds in action include two-time defending champion Stefanos Tsitsipas, fourth seed Casper Ruud and sixth seed Holger Rune, who will meet Matteo Berrettini.

View Schedule | View Singles Draw | View Doubles Draw

[3] Daniil Medvedev vs. [13] Alexander Zverev (GER)

Four weeks ago, Medvedev and Zverev contested their 13th ATP Head2Head meeting in Indian Wells, where Medvedev won a three-set thriller on his way to the final in the desert. The victory gave the 27-year-old a 7-6 edge in their long-running rivalry, which had been dormant since Zverev’s third-set tie-break win in the 2021 Nitto ATP Finals title match.

Incredibly, the two have never met on clay courts despite their long history. The change of surface will make for an intriguing tactical battle, with Medvedev previously saying that he needed to make adjustments to his favoured flat baseline strokes to succeed in the slower conditions.

Zverev, who is more comfortable playing with shaped groundstrokes, said he was playing the best clay-court tennis of his life last year at Roland Garros before sustaining an ankle injury against Rafael Nadal in the semi-finals. In his Paris run, the German excelled at using heavy spin to open up the court with angles. While Medvedev’s length and movement will make that tougher, Zverev will be eager to test his opponent’s defence in Monte-Carlo.

The third-seeded Medvedev has won four titles in his past five events, in addition to his Indian Wells final run, and he brought his scorching form into the clay-court season on Wednesday with a 6-3, 6-2 win against Lorenzo Sonego. He is not expecting such a straightforward scoreline against Zverev, who beat Alexander Bublik and Roberto Bautista Agut to reach the last 16.

“We’ve had some tough matches,” Medvedev said of their history. “We played for the first time maybe seven years ago on the ATP Tour, and in juniors maybe 12 years ago. I remember I beat him once in a final on clay in juniors, but it’s going to be a different story.

“I saw him in the first two matches, he seemed to be in good shape. I’m just going to have to be at my best.”

[1] Novak Djokovic (SER) vs. [16] Lorenzo Musetti (ITA)

Djokovic and Musetti meet for the fourth time and just the second time on clay. Their first ATP Head2Head meeting came in a memorable fourth-round match at Roland Garros in 2021, when the Serbian recovered from losing two tie-breaks and came back from two sets down to advance after Musetti retired in the fifth set.

While Djokovic swept all four sets they played in 2022 with wins in Dubai and at the Rolex Paris Masters, Musetti has been doing some sweeping of his own in Monte-Carlo. The Italian enters the third round after winning three straight 6-0 sets; he followed a 7-6(1), 6-0 win against Miomir Kecmanovic in the opening round with a double bagel against countryman Luca Nardi on Thursday.

In order to keep his winning streak in tact, the 21-year-old will need to stay on the attack against Djokovic. If Musetti can keep the Serbian on his heels and prevent him from settling into the match, he could benefit from the World No. 1’s monthlong spell on the sidelines prior to Monte-Carlo.

In his first competitve action since he lost to Medvedev in the Dubai semis on 3 March, Djokovic eased back into the win column with a 7-6(5), 6-2 result against qualifier Ivan Gakhov to begin his Monte-Carlo campaign.

“It was probably, if you can call it this way, an ugly tennis win for me today,” the Serbian assessed. “I haven’t played my best, particularly in the first set. And I kind of expected that that was going to happen in a way with swirly conditions, a lot of wind today, changing directions.

“It’s different practising and then playing an official match on clay, [where] I guess no two bounces are the same. It’s always quite unpredictable what’s going to happen. But all in all, I’m just pleased with the way I held my nerves I think in the important moments and I managed to clinch the two-set win.”

[7] Jannik Sinner (ITA) vs. [10] Hubert Hurkacz (POL)

Recent Miami finalist Jannik Sinner and 2021 Miami champion Hubert Hurkacz, who beat the Italian to claim his first ATP Masters 1000 title in South Florida, reached the Monte-Carlo last 16 in contrasting ways.

While Sinner played just 10 games and led Diego Schwartzman 6-0, 3-1 before the Argentine retired, Hurkacz has grinded through six tight sets in his two Monaco matches. The Pole was a 6-7(5), 7-6(5), 7-6(5) winner against Laslo Djere in the first round and a 6-3, 6-7(3), 7-5 victor against Jack Draper on Tuesday.

In the pair’s first clay-court match, Sinner will seek to use his all-court game to level their ATP Head2Head series at 2-2. Both men reached the Monte-Carlo quarter-finals last season, but only one will be among the last eight this year.

While Sinner made at least the semi-finals at each of the year’s first two ATP Masters 1000s in Indian Wells and Miami, Hurkacz is bidding to advance beyond the third round at that level for the first time since his final run last year in Montreal.

Also In Action…

In addition to the three matches above, Tsitsipas rounds out the action on Court Rainier III with his matchup against Nicolas Jarry. Like Sinner, the Greek was not on the court long in his opening match. He built a 4-1 lead against Benjamin Bonzi on Tuesday before the Frenchman retired with a wrist injury, while Jarry backed up an opening-round upset of 15th seed Borna Coric with a three-set win against Alexei Popyrin on Wednesday.

Rublev and Khachanov will meet for the first time since 2021 on Court des Princes after teaming up to reach the doubles second round in Monte-Carlo. Rublev came from behind for a 4-6, 6-2, 6-2 win against Jaume Munar on Tuesday, and Khachanov has not lost a set this week in victories against Alejandro Davidovich Fokina and Ilya Ivashka.

Also on Monte-Carlo’s second stage, Ruud meets Jan-Lennard Struff, Fritz faces Australian Open quarter-finalist Jiri Lehecka and Rune takes on Berrettini for their third meeting.

Three second-round doubles matches are also on the Thursday slate, including second seeds Rajeev Ram and Joe Salisbury’s meeting with Monegasque Romain Arneodo and Austria’s Sam Weissborn.

Third seeds Marcelo Arevalo and Jean-Julien Rojer survived an early scare Wednesday at the Rolex Monte-Carlo Masters. Top seeds Wesley Koolhof and Neal Skupski also avoided an upset in their clay-season opener.

The El Salvadoran-Dutch duo of Arevalo and Rojer saved seven of eight break points faced to oust Stefanos Tsitsipas and Petros Tsitsipas 6-2, 6-7(5), 10-5 in the second round of the ATP Masters 1000 event.

Two-time titlists this season (Delray Beach, Adelaide-2), Arevalo and Rojer will next meet Kevin Krawietz and Tim Puetz in the quarter-finals after the German pair cruised to a 6-4, 6-3 victory against Rohan Bopanna and Matthew Ebden.

Arevalo and Rojer were semi-finalists in Monaco last season two months before claiming their maiden Grand Slam trophy at Roland Garros, which helped them qualify for the 2022 Nitto ATP Finals.

Koolhof and Skupski were on the brink of defeat Wednesday, but the Dutch-British duo fended off four match points in the Match Tie-break to survive the challenge of Karen Khachanov and Andrey Rublev 6-7(5), 6-3, 14-12.

Seeking their first title of 2023, Koolhof and Skupski won 42 of 49 points off their first delivery to advance to the last eight, where they will clash against Fabrice Martin and Andreas Mies.

In first-round action, Juan Sebastian Cabal and Robert Farah downed Santiago Gonzalez and Edouard Roger-Vasselin 7-5, 6-7(2), 10-5. Wild cards Romain Arneodo and Sam Weissborn defeated Marcelo Melo and Alexander Zverev 6-2, 6-4.

After a strong clay campaign last season that saw him win his first ATP Tour title in Munich and reach his first Grand Slam quarter-final at Roland Garros, Holger Rune is up and running on the terre battue in 2023.

The Dane picked up where he left off on the surface with a 6-2, 6-4 win against Dominic Thiem on Wednesday night at the Rolex Monte-Carlo Masters.

“It’s my first match back on clay so there were a few adjustments to make. But I’m all in all happy with how I handled the situation on court,” Rune said post-match, noting the importance of keeping good depth on his strokes. “Dominic already played a couple of matches [on clay]. He’s a dangerous player. He can hit winners from anywhere in the court so I had to be sharp, move well and play well.”

Making his third appearance in Monaco, Rune is through to the last 16 for the first time. He was beaten by Casper Ruud in each of the past two editions of the event, losing in the opening round of his 2021 debut and in the second round last season.

The 19-year-old will face Matteo Berrettini or Francisco Cerundolo on Thursday, seeking his second ATP Masters 1000 quarter-final and first since he won the Rolex Paris Masters last November.

Thiem played some of his best tennis of the season to beat Richard Gasquet in the Monte-Carlo first round, and he made a strong start against Rune with a love hold on Court Rainier III. But Rune’s Top 10 level was too much for the Austrian in what was a one-sided opening set beyond that.

The World No. 9 pinned Thiem deep behind the baseline with relentless attacking, his electric forehand doing most of the damage as he rattled off five straight games from 1-2 to seal the set. Rune won all 14 of his first-serve points in the opener and finished with an 80 per cent win rate (28/35) behind his first delivery.

While Thiem raised his level in set two, landing heavy baseline blows of his own off both wings, the sixth-seeded Rune did not face a break point until his bid to serve out the match at 5-4. Staring down 15/40, he found two big serves to force deuce before clinching victory on his third match point.

“Of course there were a few moments at the end where I think he had maybe too much time to play,” Rune assessed. “But I think all in all we played on my terms and I’m happy with how I controlled most of the match.”

Rune is up one place to No. 8 this week in the Pepperstone ATP Live Rankings, a mark that would match his career high in the Pepperstone ATP Rankings — though his position is still under threat by a chasing pack led by Jannik Sinner. The Dane would move past the injured Felix Auger-Aliassime (left knee) at No. 7 in the Live Rankings by reaching the semi-finals in Monaco.

Thiem was seeking his first Top 10 win on clay since defeating World No. 1 Novak Djokovic in the 2019 Roland Garros semis, and his first Top 10 win overall since beating the Serbian at the same stage of the 2020 Nitto ATP Finals. The defeat dropped him to 4-10 on the season, with his Estoril quarter-final run last week his best result of the year.