Stan Wawrinka recovered from a set behind to overcome Maxime Cressy and set up a second-round showdown with Andrey Rublev at the Madrid Open.

Three-time grand slam winner Wawrinka, who is the oldest player in the main draw, hit back in the Spanish capital to progress 6-7 (7-3) 6-3 7-6 (7-4).

The 38-year-old won 46 of 54 first-serve points and now has a couple of days to recover before facing fifth seed Rublev, who was handed a bye to the last 32.

Roberto Carballes Baena is also through after defeating David Goffin 6-4 6-4, with Alexander Zverev up next, while Alex Molcan saw off Wu Yibing 6-2 6-4.

There was a shock elsewhere on Wednesday as Diego Schwartzman was downed in straight sets by Hugo Grenier.

Novak Djokovic has withdrawn from the Madrid Open, with the world number one struggling with an elbow injury just over a month before the start of the French Open.

The 22-time grand slam champion wore strapping on his right elbow at last week's Monte Carlo Masters, suffering a shock 6-4 5-7 4-6 defeat to Lorenzo Musetti in the third round.

Djokovic was back in action at the Srpska Open in Banja Luka this week, losing to fellow Serbian Dusan Lajovic in the quarter-finals, but he sparked concerns regarding his injury on the eve of that tournament.

Djokovic described his elbow as "not in an ideal condition" on Tuesday, though he added it was "good enough" for him to continue his preparations for Roland Garros.

On Saturday, however, it was confirmed Djokovic would not compete at the upcoming Masters 1000 event in Madrid, which he has won on three previous occasions.

Djokovic's absence from the clay-court event, which finishes just three weeks before the French Open begins, leaves the 35-year-old facing a battle to be fit for the second grand slam of the year.

Djokovic will not be the only big-name absentee in Madrid, with Rafael Nadal withdrawing earlier this week as he continues to struggle with an injury to his left hip.

With Nadal's chances of participating at the French Open also in the balance, tournament director Amelie Mauresmo said it was "hard to imagine" the event taking place without the 14-time winner.

Both Djokovic and Nadal will be targeting a record-breaking 23rd grand slam singles title if able to compete at the French Open, which will run from May 28 to June 11. 

Rafael Nadal remains unsure when he will return to action with the French Open looming after being forced to withdraw from the Madrid Open.

The 22-time grand slam champion has been struggling with a left hip issue that contributed to his second-round exit at the Australian Open in January.

Nadal pulled out of the Indian Wells Open and Miami Open, while the troublesome injury has also hampered the start of his favoured clay-court season.

Having withdrawn from the Monte Carlo Masters and Barcelona Open, the Spaniard is still not fit enough to participate in next week's Madrid Open on home soil.

And a concerned Nadal is now facing a race to be fit in time for the French Open, which begins in a little over five weeks' time.

"As you know, I suffered an important injury in Australia of the psoas [muscle]," he said in a video published on social media on Thursday.

"Initially it had to be a six-to-eight-week recovery period and we are now on fourteen. The reality is that the situation is not what we would have expected.

"All medical indications have been followed, but somehow the evolution has not been what they initially told us and we find ourselves in a difficult situation.

"The weeks are passing and I had the illusion of playing in tournaments that are the most important in my career, like Monte Carlo, Barcelona, ​​Madrid, Rome, Roland Garros. 

"For the moment, I have missed Monte Carlo and Barcelona. I will not be able to be in Madrid, unfortunately."

Nadal, who has played just four matches this season, added: "The injury still hasn't healed and I can't work out what I need to to compete. 

"I was training, but now a few days ago we decided to change course a bit, do another treatment and see if things improve to try to get to what comes next.

"I can't give deadlines because if I knew I would tell you but I don't know. This is how things are now."

Nadal won a record-extending 14th French Open title with a straight-sets victory over Casper Ruud in last year's final.

Andrey Rublev came from a set down against Holger Rune to win the Monte Carlo Masters on Sunday, his first Masters 1000 title.

Having done the same in his semi-final against Taylor Fritz, Rublev showed grit and determination to do so again in the final, eventually winning 5-7 6-2 7-5.

Rublev become only the third player in the Open Era to have comeback wins in both the semi-final and final at Monte Carlo after Ivan Lendl (1988) and Ilie Nastase (1971).

Rune started the stronger of the two and forced a break in the sixth game of the first set with two delightful drop-shot winners, only for Rublev to break straight back in the next game.

After throwing away seven of eight break point chances in the first set, it was somewhat inevitable Rublev was unable to save a crucial one on his own serve with Rune at set point, sending a return long to hand the Dane the first frame.

This was Rune's sixth ATP Tour-level final, making him the fifth teenager to pass five since 2000.

Rublev seemed determined not to make the same mistake again as he immediately broke Rune's serve in the opening game of the second set, although he did pass up two chances for a double break before Rune levelled the set at 2-2.

The heat appeared to be affecting both players' service games in a high-octane encounter, but Rublev steadied himself before breaking again and then racing to another as he comfortably secured the second set.

As Rublev had done after dropping the opener, however, Rune responded defiantly and raced out to a 3-0 lead in the decider, but after missing a chance to go 5-1 up, he was broken back as Rublev came back to 4-4.

At 5-5, a tiring Rune twice hit the net with overhead smashes and then had a double fault at break point, leading to a crucial break for the Russian, who then served out the match to clinch the title.

"I know it's tough to lose a final, but you are too freaking young, man, and already have a Masters 1000 title, so give me one time to win it," Rublev joked with a smiling Rune at the trophy presentation.

Andrey Rublev is hoping it will be third time lucky in a Masters 1000 final after setting up a title showdown with Holger Rune in Monte Carlo.

The 25-year-old Russian has 12 tournament wins to his name, but all have come at ATP 500 or ATP 250 level, respectable but lower rungs than this tier.

Rublev lost to Stefanos Tsitsipas in Monte Carlo in 2021 and to Alexander Zverev in Cincinnati in the same year, as he failed to capitalise on two chances to break his Masters 1000 duck.

Now comes another opportunity on the clay against teenager Rune on Sunday, after both men ground out tough semi-final comeback wins.

Rublev beat Taylor Fritz 5-7 6-1 6-3, while Rune fought back gallantly to overcome Jannik Sinner 1-6 7-5 7-5, with rain delays affected both matches on Saturday.

Rublev is full of appreciation for Rune's game. They met at the last-16 stage of the Australian Open in January, with Rublev winning a marathon clash in a dizzying final-set tie-break.

Their only other previous clash came indoors at the Paris Masters last November, with Rune taking that third-round match in straight sets and going on to win the title as an unseeded player, beating Novak Djokovic in the final.

Rublev said of Rune: "Holger is the guy who runs a lot, and he runs really well. He read the game really well. He's very talented.

"He has a good touch. He doesn't give you any rhythm, because as soon as he has a chance he tries to do drop shots, he tries to hit full power, goes to the net, returns and goes to the net, then serves to the net.

"He doesn't give you rhythm to put pressure on him to play your style."

Rune sees Rublev as a major threat to his prospects of a second title at this level, but the 19-year-old Dane is not short of self-belief.

"I expect for myself to push full. It's the last push, it's the last match of the tournament," Rune said. "Obviously he had three sets as well, so he must be feeling the legs a little bit, I hope.

"It's going to be great. We've played each other twice. It's one-all head to head, so it's going to be interesting, for sure.

"I've just got to stay in the moment, go for it against the best players in the world, and Andrey has been showing that for many years now, he's been top five, six for many years, so I've got to play my best. I've got to take it, because he's not going to give it to me."

Defending champion Stefanos Tsitsipas and Daniil Medvedev were both dumped out at the quarter-final stage of the Monte Carlo Masters, with Taylor Fritz and Holger Rune advancing.

Seeded second and third respectively, Tsitsipas and Medvedev began Friday as the tournament's highest-ranked players following Novak Djokovic's shock exit, but both found themselves on the receiving end of comprehensive defeats.

World number three Tsitsipas was the victim as Fritz claimed his first victory over a top-10 ranked player on clay, ending the Greek's 12-match winning run at the competition with a 6-2 6-4 success.

Tsitsipas – who won the event in both 2021 and 2022 – was unable to contain Fritz as the American hit a series of huge winners en route to his third Masters 1000 semi-final.

Fritz will face Andrey Rublev in the final four after the fifth seed saw off the challenge of German qualifier Jan-Lennard Struff, posting a 6-1 7-6 (7-5) win.

Meanwhile, Medvedev came up short in his tussle with Rune, as the 19-year-old waltzed into his second Masters 1000 semi-final with a 6-3 6-4 triumph.

"It wasn't easy for sure, it's always tough to play Daniil," Rune said after his win. "It was actually my first time playing against him in a real match, but we've practised tonnes of times. 

"I have huge respect for everything he's done. In the last week it was not easy to stop him, but I'm happy I managed to do it."

Rune now has a 10-8 record in meetings with his fellow top-10 players, and he will have to win another such duel to make the final, with Jannik Sinner his semi-final opponent.

Sinner needed 76 minutes to beat fellow Italian Lorenzo Musetti 6-2 6-2, and the 21-year-old now has the chance to reach his third Masters 1000 final, having previously finished as runner-up at two editions of the Miami Open.

Novak Djokovic was "not really in the mood to speak" after suffering a jarring early defeat at the Monte Carlo Masters, but insisted he would bounce back.

The 35-year-old world number one was playing his 50th main-draw match at the tournament, but it did not go to plan as he lost 4-6 7-5 6-4 to Italian Lorenzo Musetti on Thursday.

Djokovic's post-match reaction exposed huge frustration, with his first competitive outing in over a month ending at the last-16 stage.

He was forced to miss the Indian Wells and Miami tournaments last month, being denied permission to enter the United States due to his refusal to accept a COVID-19 vaccination.

Hopes he had of a long run on the Monte Carlo clay have been scuppered, but the Serbian has plenty of time to find form in time for the French Open, which begins on May 28.

Defeat marked the first time Djokovic had failed to reach the quarter-finals in a tournament since last year's Monte Carlo event, when he lost his opening match to Alejandro Davidovich Fokina.

The loss to Musetti included an argument with the umpire over a line call, while Djokovic also smashed a racket in frustration at one point.

"The feeling is terrible after playing like this, honestly," Djokovic said. "But congrats to him. He stayed tough in important moments, and that's it.

"You always hope for the good day in the office, but 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.

"I don't think it's catastrophic, but my feeling is bad right now because I lost the match. It's not a great day for me, so I'm not really in the mood to speak."

Djokovic is a two-time former winner of the ATP 1000 event but has not reached the semi-final stage since 2015, the year he was last champion.

He continues his clay campaign at a low level tournament next week in Banja Luka, Bosnia and Herzegovina.

Musetti moved on to face fellow Italian Jannik Sinner in the quarter-finals. Victory over Djokovic made Musetti the first Italian man to beat the world number one in Monte Carlo since 1973, when the ATP rankings began.

Rafael Nadal has confirmed he will not be competing at the Monte Carlo Masters.

Nadal, who has won 11 times in Monte Carlo, had been hoping to make his return from a hip injury at the ATP Masters 1000 event, which starts next week.

The 36-year-old has not played since going out to Mackenzie McDonald in the second round of the Australian Open in January.

Nadal previously cast doubt on his status for Monte Carlo last month, and on Tuesday he announced he will be unable to participate.

"Hi everyone, I'm still not ready to compete at the highest level," Nadal tweeted.

"I will not be able to play in one of the most important tournaments of my career, Monte Carlo.

"I am not yet in a position to play with the maximum guarantees and I continue my preparation process, hoping to return soon."

Nadal's latest setback is another blow in his preparations for the French Open, which starts at the end of May.

The Spaniard, who dominated in Monte Carlo between 2005 and 2012, has slipped down to number 14 in the ATP world rankings.

Daniil Medvedev won his fourth title of the 2023 season but claimed Sunday's Miami Open was the biggest one yet after knocking over Jannik Sinner 7-5 6-3 in the decider.

Medvedev improved his outstanding season record to 29-3, well ahead of the next best Sinner (21-5) with the straight-sets triumph. The Russian will rise to number four in the ATP world rankings on Monday.

The Miami title comes after the 27-year-old lifted crowns in Dubai, Doha and Rotterdam and reached the Indian Wells Open final, only to lose to top-ranked Carlos Alcaraz. During that run, Medvedev has an overall record of 24-1.

Despite Medvedev's remarkable form, Miami was his first ATP Masters 1000 title since winning the Canadian Open in Toronto in 2021.

"I haven't won such a big title in probably a year and a half," Medvedev said. "At the end I was quite shaky. Not even tight, because I'm not scared to win. But still the hands get a little shaky so the serve is a little bit tougher… I managed to get myself together and close the match.

"It's the best start of the season I have ever had. Amazing amount of points won. I think 2019 was great also with six finals and it was also new for me in 2019. So I think it's kind of the same." 

Medvedev triumphed in one hour and 34 minutes, although the contest was closer than the scoreline suggested, with both players hitting 27 winners and 14 unforced errors each.

The Russian was impressive on serve, winning 86 per cent of first serve points, but he also committed six double faults with nine aces.

"I'm really happy," Medvedev said. "Today was a tough match. It was probably the hottest day and the most humid during the day.

"It was not easy conditions. I don't know if Jannik had a small injury or cramp. I was also struggling, tried not to show it."

Medvedev is the first male to reach consecutive ATP 1000 finals since Novak Djokovic in 2020. The Russian's other ATP 1000 titles include Paris in 2020, Shanghai in 2019 and Cincinnati in 2019.

The 2021 US Open winner has also claimed 16 ATP tournament titles on hard courts since 2019, ahead of Djokovic (14) and Andrey Rublev (10) during that period. The ATP Tour now moves to clay courts.

"Generally I love hard courts," he said. "I love playing on it. If it would be my choice, it would be only hard courts, but I completely understand that that's not fair, if we can say like this. I feel the best at my game on hard courts."

Daniil Medvedev extended his perfect record against Jannik Sinner to six matches after defeating him 7-5 6-3 in Sunday's Miami Open final.

Medvedev also beat Sinner in February's Rotterdam Open final, marking his fifth win from their fifth meeting, and by improving that to 6-0 it means it is the Russian's equal-best record against a single opponent, along with Felix Auger-Aliassime and Diego Schwartzman.

Sinner had a great opportunity to take the first set, creating five break point opportunities compared to Medvedev's three, and he kept his service games clean with no double faults while Medvedev racked up four.

The 21-year-old Italian could have forced a tiebreaker in the first set, but failed to hold his serve at 6-5 down, and Medvedev capitalised on the momentum to grab an immediate break to start the second frame.

To Sinner's credit, he snatched the break right back, but Medvedev got another and safely served it out the rest of the way.

The writing was on the wall after the first set, as Medvedev came into the contest a perfect 24-0 this season when securing the opener, and the title is his 16th on hard courts since 2019, two more than second-placed Novak Djokovic (14) over the span.

It is his 19th singles title overall – at a 19th different tournament – and after a brief rough patch getting over the line, he has become one of the sport's great finishers. 

From November 2021 through June 2022 he lost five finals in a row, but he has since won six of his past seven, claiming his fifth Masters 1000 crown in the process.

Jannik Sinner is through to the Miami Open decider after eliminating world number one Carlos Alcaraz 6-7 (4-7) 6-4 6-2 in Friday's semi-final.

Sinner, 21, has enjoyed a terrific start to 2023. Since the beginning of the Australian Open, the Italian has only lost three matches – to Stefanos Tsitsipas, Daniil Medvedev and Alcaraz.

He avenged his defeat to Tsitsipas with a straight sets win at the Rotterdam Open, and he has now got one back on Alcaraz after their three-hour war of attrition.

Both players created exactly 12 break point opportunities, and Sinner's 26 unforced errors were only one less than Alcaraz's 27, but the Spanish 19-year-old committed an uncharacteristic nine double faults. The loss snapped Alcaraz's 10-match winning streak.

The victory gives Sinner his second appearance in the Miami Open final after losing the 2021 edition to Hubert Hurkacz, and he now joins Rafael Nadal and Novak Djokovic as the only players to ever reach the final here twice before turning 22.

Sinner will get a chance to avenge his only other loss this year in the final after Daniil Medvedev booked his spot with a 7-6 (7-5) 3-6 6-3 victory over Russian compatriot Karen Khachanov.

Incredibly, Khachanov lost despite hitting 53 winners and only 11 unforced errors, and he ended up edging the total point count 93-88, but he could only convert two of his six break point opportunities, while Medvedev converted two out of four.

The win means Medvedev is the first player since Roger Federer in 2019 to reach the final of both the Indian Wells Open and the Miami Open in the same season, and he is the first since Federer in 2006 to reach five ATP finals before the clay court season begins.

World number one Carlos Alcaraz made it 10 wins in a row in Miami and kept alive his hopes of a rare Sunshine Double as he beat Taylor Fritz in straight sets in Thursday's quarter-finals.

Alcaraz swept aside the 2022 Indian Wells champion 6-4 6-2 in a lopsided Miami Open contest which lasted only 79 minutes, with the Spaniard breaking Fritz in the opening game of both sets.

Both players hit 20 winners, including 11 each on their respective forehands, but Fritz almost doubled Alcaraz' unforced errors count (28-13).

The 19-year-old was impressive from the baseline and overwhelmed Fritz in the end. The American only won 38 per cent on his second serve.

Alcaraz, who won the Indian Wells title a fortnight ago, remains on track to become the eighth male to win the Sunshine Double (Indian Wells and Miami), with Roger Federer the last to achieve that in 2017.

The Spaniard would join Federer (2005, 2006, 2017), Novak Djokovic (2011, 2014, 2015, 2016), Andre Agassi (2001), Marcelo Rios (1998), Pete Sampras (1994), Michael Chang (1992) and Jim Courier (1991) in achieving the Sunshine Double.

Alcaraz will take on Italian 10th seed Jannik Sinner in the semi-finals, after the duo faced off in the Indian Wells last four a fortnight ago, with the Spaniard winning in straight sets.

In-form Daniil Medvedev progressed to the semi-finals with a 6-3 7-5 victory over American qualifier Chrstopher Eubanks, who had enjoyed a dream run in Miami.

Medvedev has a 27-3 record this season and will pursue a fifth straight ATP Tour final when he takes on compatriot Karen Khachanov in the semi-finals.

Khachanov, who made this year's Australian Open semi-finals, defeated Francisco Cerundolo 6-3 6-2 in 76 minutes.

Italian 10th seed Jannik Sinner downed Emil Ruusuvuori to secure his berth in the Miami Open semi-finals along with bringing up his 20th win of the season on Wednesday.

Sinner, who dropped only one point on first serve, won 6-3 6-1 over the Finn in one hour and 16 minutes.

The 21-year-old Italian will face either top seed and defending champion Carlos Alcaraz or 2022 Indian Wells winner Taylor Fritz in the last four. Sinner lost to Alcaraz in the Indian Wells semi-finals a fortnight ago.

Alcaraz and Fritz's Miami quarter-final was postponed to Thursday with persistent rain forcing the evening session in Miami to be cancelled.

The other quarter-finals between 14th seed Karen Khachanov and 25th seed Francisco Cerundolo along with fourth seed Daniil Medvedev and qualifier Christophr Eubanks were also re-scheduled for Thursday.

The Sinner-Ruusuvuori clash was also impacted by a two-hour rain delay, but the Italian prevailed to maintain his perfect record in Miami, having not dropped a set.

"We both played well today but I won the important points," Sinner said. "It's never easy when you are up and you get interrupted, but I came back and played well."

Sinner's run to the Miami semi-finals has seen him drop the fewest games (23) since Rafael Nadal (21) and Novak Djokovic (23) in 2014.

The Italian became the seventh male to reach the semi-finals at both Indian Wells and Miami in a single year before turning 22, joining an elite list in Andre Agassi (1990), Jim Courier (1991), Djokovic (2007), Andy Murray (2007 and 2009), Nadal (2008) and Alcaraz (2022).

Sinner's 2023 record is now 20-4, bettered only by Medvedev (26-3) and Cameron Norrie (21-5).

Carlos Alcaraz does not disagree with Novak Djokovic's assertion of being the best player in the world, as the Spaniard outlined his hope of facing the 22-time major winner at full fitness.

Alcaraz has played Djokovic once before, overcoming the Serbian en route to triumphing at last year's Madrid Open.

The teenager's success in Madrid marked his fifth tour-level title, and his second at an ATP 1000 event.

Earlier in March, Alcaraz claimed his third ATP 1000 title with victory at the Indian Wells Open, seeing the 19-year-old leapfrog Djokovic – who has been unable to compete in the United States due to his COVID-19 vaccination status – back to the top of the world rankings.

Djokovic claimed in interview with The National in February that he was still the best player in the world when at 100 per cent fitness.

Alcaraz, for his part, shares that view.

"Well, it is tough one, but, I have to play against Novak when he's at 100 per cent," Alcaraz told reporters after beating Tommy Paul at the Miami Open, where he is defending champion.

"I would say in Madrid he played really, really well. So it was close. But I agree with him. When he's 100 per cent, probably the best player in the world.

"What Novak has achieved, the level of Novak for example in Australia was unbelievable, really high.

"So as I said before, I really want to play against Novak when he's 100 per cent and I'm sure I'm going to enjoy it. That's all I can say right now."

Alcaraz remains on course for the Sunshine Double – winning both the Indian Wells Open and Miami Open in the same season.

"I try not to think about that but it's difficult," he said. "You know, it's something that I really want. I want to be part of the few players that won the Sunshine Double.

"So for me, would be great to achieve that, but it's something that I try not think about and try to think about day by day, match by match, and that's all. 

"But of course it could be great to be part of that group of few players."

Eleven players, including Djokovic – on four occasions – have won the Sunshine Double, with WTA number one Iga Swiatek the latest to achieve the feat last season.

Second seed Stefanos Tsitsipas was bundled out of the Miami Open in straight sets during Tuesday's fourth round by 2022 US Open semi-finalist Karen Khachanov.

The Russian 14th seed prevailed 7-6 (7-4) 6-4 over Tsitsipas in one hour and 34 minutes, powering 25 winners and making only nine unforced errors, compared to the Greek's 14.

Khachanov's triumph ended a winless 0-6 head-to-head record against Tsitsipas, while it also snapped his own 23-match losing streak against top-10 opponents.

The Russian, who also made this year's Australian Open semi-finals, has qualified for four of his six tour-level events this year.

Khachanov will take on 25th seed Francisco Cerundolo in the quarter-finals, with the Argentinian fighting back to get past Lorenzo Sonego 3-6 6-3 6-2 in just over two hours.

Defending champion and top seed Carlos Alcaraz had less trouble against Tommy Paul, cruising into the quarter-finals with a 6-4 6-4 victory.

Alcaraz won the winners' count 24-9, setting up a quarter-final clash with ninth seed Taylor Fritz, as the Spanish 19-year-old chases a rare Sunshine Double, having won last week's Indian Wells Open.

Fritz progressed after getting past seventh seed Holger Rune 6-3 6-4 in 86 minutes, sending down eight aces and 22 winners for the match.

Fourth seed Daniil Medvedev played late into the evening after a lengthy rain delay in Miami, but made light work of Quinten Halys 6-4 6-2, triumphing just past 1:30am local time.

Medvedev, who is into his third straight Miami quarter-final, will face American qualifier Christopher Eubanks in the last eight after he got past Frenchman Adrian Mannarino 7-6 (7-2) 7-6 (7-5) in another rain-delayed contest.

Italian 10th seed Jannik Sinner knocked off sixth seed Andrey Rublev 6-2 6-4, advancing to face Emil Ruusuvuori after he beat Botic van de Zandschulp 4-6 6-4 7-5.