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The entirety of the remaining men's singles field will play on Tuesday at the Mutua Madrid Open, with the fourth round set to be completed over the course of a packed day at the ATP Masters 1000.

The pick of the eight matchups is a rematch of last year's Madrid final between Carlos Alcaraz and Alexander Zverev, with Top 10 seeds Andrey Rublev and Karen Khachanov also squaring off in the draw's top half. Daniil Medvedev's meeting with Aslan Karatsev is another highlight, while three Spaniards in addition to Alcaraz hope to advance to the quarter-finals, led by 29th seed Alejandro Davidovich Fokina. 

ATPTour.com looks at some of the key fourth-round matchups on the Day 9 schedule across the men’s singles draw and men’s doubles draw.

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[1] Carlos Alcaraz (ESP) vs. [13] Alexander Zverev (GER)

Alcaraz dominated the 2022 Madrid final against the Zverev, capping an emphatic three-match stretch in which he defeated Rafael Nadal, Novak Djokovic and the German. That victory clinched a trophy double for the Spaniard across Barcelona and Madrid, and the 19-year-old is now four wins away from repeating that feat this season. If he does claim the title, Alcaraz would be guaranteed to return to No. 1 the week after Rome simply by playing a match in the Italian capital.

Roger Federer returned to the Met Gala on Monday for the first time since 2017, when he intrigued fans worldwide in a crystal cobra on his tuxedo.

Federer wore a less adventurous outfit on Monday evening, but the GQ’s Most Stylish Man of the Decade was in his element in at The Metropolitan Museum Of Art.

Earlier in the day, the Swiss legend joined friend and Editor in Chief of Vogue Anna Wintour for a look at The Costume Institute's exhibition — Karl Lagerfeld: A Line of Beauty.

Photo Gallery: AFP/Getty Images
Federer enjoyed his time in New York ahead of the Met Gala. The Swiss visited the Cary Leeds Center to speak with local junior players. He also caught up with comedian Trevor Noah.

A ?of home in the Big ???@Trevornoah pic.twitter.com/3fLhmJcoLq

China's Zhang Zhizhen backed up his upset of Denis Shapovalov with an even bigger win against Cameron Norrie on Monday at the Mutua Madrid Open. Both triumphs came via a third-set tie-break, with the 26-year-old battling back to stun Norrie 2-6, 7-6(2), 7-6(2) and notch his first Top 20 win.

"Before the match I didn't even think I was going to be here in the second week of Madrid," the Shanghai native said after extending his dream debut at the ATP Masters 1000. "Now I made it!

"This is a big victory because it was an amazing match. The first set was tough, I was down 6-2 but I still didn't give up. And then I won two tie-breaks, that's amazing. Normally my tie-breaks is losing one and then win. So today I had two wins, that's unbelievable really."

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Zhang, who became the first Chinese player to break into the Top 100 of the Pepperstone ATP Rankings last October, has moved up 10 places to No. 89 in the Pepperstone ATP Live Rankings behind his best run at an ATP Masters 1000 — a mark that would represent a new career high. With a win in his last-16 match against Taylor Fritz, he could rise as high as No. 65.

"Again, a top player for sure, a tough match," Zhang said of the his third straight seeded opponent. "I will try to be my best, try to fight."

After edging Dominic Thiem in a third-set tie-break to open his Mutua Madrid Open campaign, Stefanos Tsitsipas again owned the clutch moments in a Monday win against Sebastian Baez. In a 7-5, 3-6, 6-3 victory, the Greek rattled off the final four games of the opening set and the last three of the third to advance to the last 16 at the ATP Masters 1000.

"He made it very difficult for me. Honestly, it was demanding in a lot of ways. I had to bring the best out of my game," Tsitsipas said post-match. "He wasn't missing much. Of course he's someone that covers and runs around the court pretty well. He definitely utilised that pretty well against me, being able to navigate himself throughout the entire court with ease, just gliding through the court like a cheetah."

Emerging victorious from the Madrid jungle, Tsitsipas improved to 8-2 on clay this season as he continues his bid to return to the semi-finals at the event for the third time. A 2019 finalist in the Spanish capital, he also reached the last four in 2022. If he can win his third ATP Masters 1000 title this week, he could rise as high No. 3 in the Pepperstone ATP Rankings and move within 1,000 points of World No. 1 Novak Djokovic.

A trophy would be his first of the season following defeats in the final at the Australian Open and last week in Barcelona.

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Andy Murray playing Gael Monfils is worthy of a Grand Slam quarter-final. Indeed Murray toughed out a five-set victory in the Roland Garros quarters when he last met the Frenchman almost nine years ago.

So fans at this week’s ATP Challenger 175 event in Aix-en-Provence, France are in for a treat when two of the most popular players in the modern game face off in the first round of the Open Aix Provence Credit Agricole.

And Murray and Monfils are not the only big-name stars who will be in Challenger Tour action this week. Several high-ranked players who lost early at the Mutua Madrid Open will now have an opportunity to make a splash at one of two 175 events this week in Aix-en-Provence and Cagliari, Italy.

At the Sardegna Open in Italy, Yoshihito Nishioka, Ben Shelton, and Mackenzie McDonald are the top three seeds. Diego Schwartzman, Thanasi Kokkinakis, and Ugo Humbert will also be in Cagliari.

Thanasi Kokkinakis greets fans at the Sardegna Open in Cagliari, Italy. Credit: Mike Lawrence/ATP Tour

Match Tie-break fever took hold in the doubles draw Monday at the Mutua Madrid Open.

All three second-round matches that took place were settled in a decider at the clay-court ATP Masters 1000. Among the teams that triumphed in the Spanish capital were Rohan Bopanna and Matthew Ebden, who edged Marcelo Melo and Alexander Zverev 6-4, 1-6, 10-5.

Bopanna and Ebden finished with a flourish on Court 4, winning the final five points of the match to clinch a 75-minute win and keep alive their bid for their second Masters 1000 title of the season.

The Indian Wells champions Bopanna and Ebden will take on Wesley Koolhof and Neal Skupski in the quarter-finals, after the top seeds pulled through 4-6, 6-4, 10-5 against home wild cards Roberto Carballes Baena and Martin Landaluce.

Singles stars Karen Khachanov and Andrey Rublev also delivered a strong finish to book their quarter-final berth. Taking on four-time Masters 1000 titlists Nikola Mektic and Mate Pavic, Khachanov and Rublev saved all four break points they faced in their 6-7(5), 6-3, 10-6 triumph. They next face Jamie Murray and Michael Venus.

The ATP Challenger Tour prides itself in providing a raw look into professional tennis, offering an opportunity for fans to watch players go from grind to glory.

Indian Sumit Nagal is a case in point. The 25-year-old returned to the Challenger Tour winners’ circle Sunday following a difficult journey.

Nagal advanced through qualifying at the Roma Garden Open and went on a dream run, downing Dutchman Jesper de Jong 6-3, 6-2 in the final.

Nagal, who is one of five Challenger champions this week, captured his third Challenger title and first since 2019. Nagal’s journey since claiming the Buenos Aires Challenger four years ago has been filled with challenges, including undergoing right hip surgery in 2021. But this week on the Italian clay courts came with a great reward.

“It always feels good to lift a trophy, especially when it’s been four years since you won your last one,” Nagal wrote in an Instagram post following the Rome Challenger title. “There were times when the days were cold and the cards all fold.

Chasing his maiden ATP Tour title on clay at the Mutua Madrid Open, Taylor Fritz demonstrated his recent improvement on the surface Monday with a scintillating 6-1 7-6(4) third-round triumph against Cristian Garin.

The American marked his coach Michael Russell’s birthday with a lights-out performance on Arantxa Sanchez Stadium, where he struck the ball cleanly on serve and off the ground throughout his 92-minute victory. The No. 10 in the Pepperstone ATP Rankings, Fritz fired 26 winners and held his nerve after Garin forced a second-set tie-break to reach the last 16 in Madrid for the first time in three appearances.

Now 7-2 for the year on clay, the Monte-Carlo semi-finalist Fritz will take on Cameron Norrie or Zhang Zhizhen as he chases his second ATP Masters 1000 title.

More to follow…

Challenger TV is your home for all the action on the ATP Challenger Tour. You can watch free live streams and full match replays of your favourite players and tournaments.

All the live matches and replays can be found on the Challenger TV landing page. You can learn all you need to know about the Tour on the ATP Challenger Tour Landing Page. Watch ATP Challenger Tour videos, read Challenger news and more throughout ATPTour.com (find info for app users below).

The ATP Challenger Tour is the launchpad of men's professional tennis. The Challenger Tour calendar features 200 tournaments across more than 40 countries each season. At this level, players develop their skills and earn valuable experience against strong competition, while fighting for critical points and prize money, all with the collective goal of progressing onto the ATP Tour.

Since it was founded in 1978, the ATP Challenger Tour has been an intense battleground on a global stage, providing fans the opportunity to witness world class tennis and follow the journeys of the stars of tomorrow as they launch their professional careers.  

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Daniil Medvedev added a second triumph to his 2023 Mutua Madrid Open campaign on Monday, but not before the second seed was given a real scare by qualifier Alexander Shevchenko at the clay-court ATP Masters 1000 event.

Medvedev twice rallied from a break down in the deciding set to claim a tense 4-6, 6-1, 7-5 win on Manolo Santana Stadium. He was forced to call on all his renowned defensive abilities to keep the 22-year-old Shevchenko at bay, but held firm in the Madrid heat to seal a two-hour, 43-minute triumph.

“He played well. He’s young, so I’m sure he’s going to up the rankings, especially if he plays like in this tournament,” said Medvedev of Shevchenko, who has risen five spots to No. 91 in the Pepperstone ATP Live Rankings as a result of his run to the third round on his Masters 1000 main-draw debut. "It’s always like this. He’s still young so he has a lot of time to go up.

“I practised with him before, I know that he can play very good, so the more consistent he is [and] the more matches he plays like this, maybe next time he’s going to win and the higher he is going to go. I’m very happy that today I managed to beat him.”

Shevchenko made a lightning start to his first match against a Top 10 opponent. The 22-year-old forged an ultimately unassailable 5-1 lead in the first set but soon found himself 0-5 down in the second as Medvedev began to counter his opponent’s high-class shotmaking with typical resilience from the baseline.

Monday's action at the Mutua Madrid Open will finalise the last 16 at the ATP Masters 1000, with the third round to be completed on Day 6 of main-draw play. Second seed Daniil Medvedev will start the day's slate in Manolo Santana Stadium against Alexander Shevchenko, with fourth seed Stefanos Tsitsipas meeting 25th seeed Sebastian Baez in the evening session on centre court.

Taylor Fritz's midday matchup with Cristian Garin headlines the action in Arantxa Sanchez Stadium, with Frances Tiafoe facing Pedro Cachin just before on Madrid's second stage.

ATPTour.com looks at some of the key third-round matchups on Monday's schedule across the men’s singles draw and men’s doubles draw.

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[2] Daniil Medvedev vs. [Q] Alexander Shevchenko

A self-proclaimed "hard-court specialist", Medvedev has found his footing on the clay this season with a quarter-final run in Monte-Carlo and a confident performance in a 6-4, 6-3 win against Andrea Vavassori in the Madrid opening round. 

The admiration for Carlos Alcaraz in the world of sports knows no bounds. On Sunday, several Real Madrid players made the trip to Manolo Santana Stadium to cheer on the Spaniard during his third-round clash in the Mutua Madrid Open.

The Murcia native, a self-confessed fan of the Whites, enjoyed the special support from courtside. Real Madrid players Vinicius Junior, Fede Valverde, Dani Ceballos and Rodrygo were among those who watched the defending champion’s match against Grigor Dimitrov of Bulgaria.

Just 19 years of age and a huge football fan, Alcaraz was delighted to have them on his side.

“I still get nervous, I’m not going to lie”, admitted Alcaraz, who had the chance to say hello to the players before leaving for the locker room. “Seeing giants like them in the stands… I’m so happy that they would come to see my match.”

The No. 2 player in the Pepperstone ATP Rankings took the chance to wish the Real Madrid players good luck for the next few weeks, when they will face one of the biggest challenges of the season in their Champions League semi-final. 

Alejandro Davidovich Fokina rode the support of his home crowd to a stirring upset of sixth seed Holger Rune on Sunday at the Mutua Madrid Open. With victory in a 7-6(1), 5-7, 7-6(5) battle of attrition, the Spaniard earned his fourth Top 10 win by outlasting Rune over the course of three hours, five minutes on Manolo Santana Stadium.

Both players received treatment during the dramatic match — Rune for his right wrist early on, and Davidovich Fokina for his upper leg area late — and struggled physically at times, but it was the Spaniard who summoned the energy in the decisive tie-break to progress to the last 16.

"Mentally and physically it was very hard," Davidovich Fokina said after the post-1 a.m. finish. "Rune is a very good player. It was always tough games and we had to stay focussed on every service, because you never know when you [can] have the break point.

"I had my chances in the third set too, but I had a lot of tension and I was a little bit anxious to finish the point," added the 23-year-old, who let slip a 5-3 lead in the decider before regrouping. "But I did well and I'm very happy."

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Davidovich Fokina is bidding to advance to a second ATP Masters 1000 final after he earned two of his Top 10 wins in reaching the Monte-Carlo title match last season, beating Novak Djokovic and Matteo Berrettini in Monaco.

After escaping Emil Ruusuvuori in a three-set comeback to begin his title defence at the Mutua Madrid Open, Carlos Alcaraz advanced to the last 16 with a thoroughly entertaining win on Sunday against Grigor Dimitrov. In a 6-2, 7-5 victory, the stylish Alcaraz imposed his athletic game to make a fast start then showed his grit to instantly recover a break in the second set.

He will next face Alexander Zverev in a rematch of last year's Madrid final, won by Alcaraz in straight sets. Zverev leads the ATP Head2Head 3-1, including a win in their most recent meeting in last year's Roland Garros quarter-finals.

"I really want to play that match. We played a few times, head-to-head he is up," Alcaraz said of the showdown encounter. "I really want to show my great level here in front of my home crowd. I have great memories from last year in the final but obviously I have to be really focussed in that match. I know that Sascha is a really good player, a really aggressive one with good serves. I have to show all my skills."

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Alcaraz is seeking to complete the Barcelona-Madrid double for the second straight season after retaining the title at the Barcelona ATP 500 last Sunday. He has won 17 straight matches on Spanish soil across four campaigns and must push that number to 21 to earn the title in Madrid.

Marcelo Arevalo and Jean-Julien Rojer overcame Americans Taylor Fritz and Frances Tiafoe 6-3, 6-4 at the Mutua Madrid Open to reach their fifth tour-level quarter-final of the season.

Chasing their third tour-level title this year, the fourth seeds won 90 per cent (28/31) of their first-serve points to move past the Top 15 singles stars and improve to 14-6 as a team on clay. Arevalo and Rojer, who triumphed at Roland Garros last season, will next face Felix Auger-Aliassime and Denis Shapovalov.

The Canadians, who advanced to the last eight in Indian Wells, downed sixth seeds Lloyd Glasspool and Harri Heliovaara 6-4, 6-2.

In other action, Jamie Murray and Michael Venus defeated Nathaniel Lammons and Jackson Withrow 3-6, 6-3, 10-4 in one hour and 21 minutes. Murray and Venus have now won six consecutive matches after lifting the trophy in Banja Luka last week.

Alexander Zverev continued his love affair with the Mutua Madrid Open on Sunday when he wasted little time in reaching the fourth round. The German overpowered French qualifier Hugo Grenier 6-1, 6-0 in 55 minutes.

Zverev survived an opening-round scare against Roberto Carballes Baena but faced no such problems against Grenier. He struck 26 winners, won 86 per cent (17/20) of net points and broke Grenier’s serve six times to earn his 12th win of the season.

"Today I felt great," Zverev said. "Maybe Hugo was a bit nervous, first time in the third round at a [ATP] Masters [1000] and that is big for any player. In general I am happy that I kept my composure and that I am through."

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The 13th seed has often produced his best level on the Madrid clay, holding a 21-3 record at the ATP Masters 1000 event. He has reached at least the quarter-finals in all five of his previous appearances, lifting the trophy in 2018 and 2021.

Players on the ATP Challenger Tour often carry impactful stories that go relatively untold.

Such is the case with Belgian Zizou Bergs, who has been donating tennis equipment to the African country Burundi for eight years. A five-time Challenger Tour champion, the 23-year-old recently triumphed at the Tallahassee Challenger just a few weeks after his grandfather passed away. Bergs’ life off the court is a story within itself.

Following an eye-opening trip to Burundi at age 15, the Belgian No. 2 quickly developed a contact, Marcel Van der Haegen, in the East African country and has since donated tennis clothes and equipment.

“I still have that project going on,” Bergs told ATPTour.com. “We're not always aware about it, but you have so much and sometimes feel like you have little. You grow up in a very good culture, in a very good country and you think everything is quite normal that you have all these clothes, shoes, racquets, you can string whenever you want, get great food at the table every day. That is not common [there], it really opened my eyes. They would play with my [stuff], even if it was like five sizes too big, they would still play with it. That really touched me.”

Earlier this month, Burundi hosted an ITF Women’s 25K event. Bergs received word from a friend at the tournament that while she was there, she noticed several guys around the capital city Bujumbura who were wearing his clothes and playing with the racquets he’s donated over the years.

Karen Khachanov reached the fourth round at the Mutua Madrid Open for the first time on Sunday when he clawed past Spaniard Roberto Bautista Agut 7-5, 4-6, 6-3 in a Madrid thriller.

Competing in front of a packed crowd inside Manolo Santana Stadium, both took large cuts at the ball as they looked to impose their powerful games. After a tight first two sets, Khachanov hit a purple patch in the decider. He struck 20 winners in the third set compared to four from Bautista Agut and won three straight games from 3-3 to triumph in two hours and 53 minutes.

Khachanov, who is making his sixth appearance in Madrid, reached the semi-finals at the Australian Open in January before he advanced to the last four at the Miami Open presented by Itau in March. The 26-year-old is chasing his fifth tour-level crown and first since 2018 this fortnight in the Spanish capital.

With his 18th win of the season, Khachanov improved to 3-6 in his long-running ATP Head2Head series rivalry against Bautista Agut. Up one spot to No. 11 in the Pepperstone ATP Live Rankings, Khachanov will next meet fifth seed Andrey Rublev.

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Third-round action begins on Sunday at the Mutua Madrid Open, where Carlos Alcaraz, Andrey Rublev and Holger Rune continue their title quests at the ATP Masters 1000 clay-court event.

Karen Khachanov, Hubert Hurkacz and Alexander Zverev also play on a day when seeded stars clash for the first time at this year’s event. ATPTour.com looks at some of the key third-round matchups on show in the Spanish capital on Sunday across the men’s singles draw and men’s doubles draw.

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[1] Carlos Alcaraz (ESP) vs. [26] Grigor Dimitrov (BUL)

Alcaraz triumphed in Madrid last year, defeating Rafael Nadal, Novak Djokovic and Alexander Zverev en route to the crown. Twelve months on and the 19-year-old overcame a tough opening test against Emil Ruusuvuori on Friday to set a second meeting against former World No. 3 Grigor Dimitrov.

Alcaraz, who will boost his World No. 1 hopes if he defends his title in the Spanish capital, is seeking his fourth tour-level title of the season in Madrid. The home favourite will be aware of the threat Dimitrov holds as he chases his 17th consecutive win at Spanish ATP Tour events.