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.
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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.”
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."
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.
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.
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.
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[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.