Rafael Nadal suffered his earliest Internazionali d'Italia exit since 2008 at the hands of Denis Shapovalov on Thursday, but Novak Djokovic advanced to the quarter-finals. 

'King of Clay' Nadal fell to a 1-6 7-5 6-2 defeat to Shapovalov in the third round in Rome, with the Canadian surging to victory after winning 12 straight points from 2-2 in the deciding set. 

The legendary Spaniard stormed through the first set thanks to a series of brilliant returns, but his opponent dominated at the net in the second to take the match the distance. 

Shapovalov then flipped the narrative on its head by winning 14 of a possible 22 return points to set up a quarter-final meeting with Casper Ruud, who beat Jenson Brooksby 6-3 6-4. 

Djokovic is one win away from retaining his status as world number one after taking just 75 minutes to see off three-time grand slam winner Stan Wawrinka 6-2 6-2. 

After a lengthy spell out injured, Wawrinka ended a 15-month wait for an ATP Tour victory at Foro Italico before the Serbian brought his run to an end. 

"It is great to see Stan back and winning. He won two tough matches. You can see he is still not physically where he wants to be. But, nevertheless, he is Stan Wawrinka and he can hurt you if you give him time," Djokovic said. 

"I managed to do well from the beginning. I really moved him around the court and held my serve comfortably except for that loss of my serve in the second set." 

Felix Auger-Aliassime stands between Djokovic and the number one spot after overcoming lucky loser Marcos Giron 6-3 6-2. 

In the other half of the draw, Stefanos Tsitsipas and Jannik Sinner will play out an entertaining quarter-final after they beat Karen Khachano and Filip Krajinovic respectively. 

Alexander Zverev, the defeated finalist in Madrid last week, beat Alex De Minaur 6-3 7-6 (7-5) and will battle Cristian Garin for a place in the final four.

Novak Djokovic had few issues seeing off Aslan Karatsev to reach the last 16 of the Internazionali d'Italia on Tuesday as he bids to remain world number one.

Djokovic needs to reach the semi-finals in Rome to ensure Daniil Medvedev cannot usurp him atop the ATP rankings next week, and he made a solid start with a 6-3 6-2 victory over another Russian in the second round.

Karatsev did initially pose a threat, with both players breaking at the first opportunity, but Djokovic's superiority gave him the edge in the first set and then saw him cruise in the second.

Djokovic – who will face either Stan Wawrinka or Laslo Djere next – acknowledged he undoubtedly benefited from Karatsev's wastefulness, however.

"You never know with him," Djokovic said. "If he's feeling the ball, he can be very dangerous because he stays so close to the line, puts pressure on his opponents.

"He was missing a lot of balls today, though. He gave me a couple of breaks there in the first and second sets, but I'll take this win for sure.

"It's a straight-sets win against a quality opponent, and I'm looking forward to the next challenge."

Fifth seed Casper Ruud also progressed to the last 16 but was tested by Botic van de Zandschulp, with the Norwegian eventually coming through 6-7 (4-7) 6-2 6-4.

But Andrey Rublev, who had won six of his previous seven matches, was a surprise second-round casualty as he fell to Filip Krajinovic in straight sets, with the Serbian claiming a 6-2 6-4 win.

Canadians Felix Auger-Aliassime and Denis Shapovalov were the other seeds to reach the last 16 on Tuesday. The former was pushed hard by Alejandro Davidovich Fokina in his 4-6 7-6 (7-2) 6-2 success, while the latter could face Rafael Nadal next up.

Meanwhile, across seven first-round matches, Cameron Norrie, Jannik Sinner and Diego Schwartzman were the biggest names to advance, though 11th seed Hubert Hurkacz was dumped out by the unseeded David Goffin.

David Goffin was impressive in his 6-4 6-2 win against Botic van de Zandschulp – earning a third round fixture against Rafael Nadal on the clay courts of the Madrid Open.

The Belgian was stronger both on serve and in the return game, winning 66 per cent of his service points compared to Van de Zandschulp's 53 per cent, and 47 per cent of his return points to the Dutchman's 34 per cent.

Goffin will face Nadal next for a place in the quarter-finals as the Spaniard searches for his first Madrid crown since 2017.

In a clash between two of the world's top-25 players, Italy's Jannik Sinner came out on top 6-4 6-1 against Australia's Alex de Minaur.

After a tight first set, which featured four consecutive breaks of serve, Sinner found another gear in the second.

He improved his service points from 53 per cent up to 80 per cent, allowing no break point opportunities for the Aussie and converting the two break points he created for himself.

Fourth seed Stefano Tsitsipas was rock-solid against France's Lucas Pouille, taking it 6-3 6-4.

The Greek won 94 per cent of his successful first serves and allowed just one break point – instantly breaking back to-love the following game.

Andy Murray swept aside Dominic Thiem in impressive fashion to secure his first clay-court win in five years as the Scot advanced to the second round at the Madrid Open on Monday.

The three-time grand slam champion was largely in control against his Austrian opponent, hitting nine aces and saving all three break points against his serve, while Thiem could only save one of the three he faced as Murray won 6-3 6-4.

He will now play 14th seed Denis Shapovalov after the Canadian beat Ugo Humbert 7-6 (7-1) 6-3.

The winner of that contest will have a last-16 meeting against the victor of Novak Djokovic and Gael Monfils after the latter eased into the round of 32 to set up a clash with the Serbian.

Monfils defeated wildcard Carlos Gimeno Valero 6-3 6-0 in less than an hour, while Alejandro Davidovich Fokina also advanced with a 7-5 6-3 win against Lloyd Harris.

Dusan Lajovic set up a second-round match against fifth seed Casper Ruud, who defeated Borna Coric 6-3 4-6 6-4, and ninth seed Cameron Norrie will go up against John Isner, the Briton having overcome Soonwoo Kwon 7-5 7-5.

An interesting tie awaits the much-talked about Carlos Alcaraz after Nikoloz Basilashvili beat Fabio Fognini 7-5 6-4, with the Georgian to face the number seven seeded teenager next.

Jannik Sinner, the 10th seed, scraped through a hard-fought encounter against American Tommy Paul 6-7 (4-7) 7-6 (7-4) 6-3, and will play Alex de Minaur next after the Australian beat Pedro Martinez 7-6 (7-2) 1-6 6-3.

Diego Schwartzman will take on Grigor Dimitrov in the second round. The Argentine 13th seed beat Benoit Paire 6-2 6-7 (5-7) 6-1, while Dimitrov overcame Maxime Cressy 6-2 7-6 (7-4).

Reigning Monte Carlo Masters champion Stefanos Tsitsipas will have to overcome Alexander Zverev if he is to have the chance to defend his title.

Zverev, who is ranked third in the world - two places higher than Tsitsipas - fought back to defeat Jannik Sinner 5-7 6-3 7-6 (7-5) in his quarter-final match, denying his opponent another top-five seed scalp following his prior win over Andrey Rublev.

"It means a lot, definitely, especially [with] how this year has been going so far for me," said Zverev after a gruelling three hours on court.

"I've lost long matches like that, so I’m happy I won this one."

Tsitsipas also orchestrated a superb turnaround against Diego Schwartzman, prevailing 6-2 6-7 (3-7) 6-4.

The Greek had looked set for a last-eight exit at four games down in the final set, only to stage a dramatic comeback to keep his hopes of a first title since last May's Lyon Open alive.

"There was a moment in the match where I felt what I was doing wasn't working," Tsitsipas said.

"He had a massive lead and momentum in what he was trying to do. I just tried to stay in the match as much as I could and that worked out very well.

"I wasn't expecting much at that point being a double break down, so I relaxed at that point."

Schwartzman meanwhile will rue his inability to put the tie to bed, having already reached two ATP finals this year.

Grigor Dimitrov and Alejandro Davidovich Fokina will face off in the other semi-final.

Bulgarian Dimitrov beat off Hubert Hurkacz in another final-set tie-break, winning 6-4 3-6 7-6 (7-2).

Fokina, who eliminated Novak Djokovic in the second round, turned over Indian Wells champion Taylor Fritz in another comeback result, triumphing 2-6 6-4 6-3.

Alexander Zverev and Stefanos Tsitsipas progressed to the quarter-finals of the Monte Carlo Masters with straight sets wins on Thursday, remaining on course for a final meeting.

Last year's runner-up Andrey Rublev, however, missed out on a last-eight spot after falling to a three-set defeat against Jannik Sinner.

World number three Zverev overcame Spain's Pablo Carreno Busta 6-2 7-5 to progress in Monaco, where he is seeking to win the sixth ATP 1000 title of his career.

"For the second clay-court match of the season, I can't complain too much," the 24-year-old second seed said on court after sealing the victory.

"Yes, I lost focus a little bit in the second set, but at the end of the day, he's somebody that can really play. I'm happy with a two-set win."

Tsitsipas (3) remains in contention for a second consecutive title in the principality after defeating Laslo Dere 7-5 7-6 (7-1) and will face off against 12th seed Diego Schwartzman for a semi-final spot after the Argentine defeated Lorenzo Musetti in a hard-fought three-set encounter.

There will be no repeat of 2021's final between Tsitsipas and Rublev, however, after the Russian fell to a thrilling 5-7 6-1 6-3 loss to ninth seed Sinner in the day's final contest.

The other seed to fall victim to a shock in the last 16 was world number seven Casper Ruud, losing 6-3 7-5 to Grigor Dimitrov, who will face Poland's Hubert Hurkacz in the last eight. 

Finally, Novak Djokovic's conqueror Alejandro Davidovich Fokina cruised past David Goffin 6-4 6-1 to set up a quarter-final tie with the United States' Taylor Fritz, who bested compatriot Sebastian Korda – with whom he played doubles with in Monte Carlo – in straight sets.

Stan Wawrinka's ATP Tour return at the Monte-Carlo Masters ended in defeat, while Jannik Sinner came through a tense encounter with Borna Coric. 

The former world number three made his comeback after more than a year out with a left foot injury that required two surgeries but fell to a 3-6 7-5 6-2 defeat to Alexander Bublik in the first round. 

Wawrinka, who entered the tournament as a wildcard having slipped to 236 in the world rankings, came from a break down to take the opening set but fatigue eventually set in and he was eliminated after two hours and seven minutes. 

"I think the body's getting much better," said Wawrinka, who lost in straight sets to Elias Ymer at a Challenger tournament in Marbella two weeks ago. 

"I'm still far away from where I want to be, but I think I'm [going in] the right direction. I think today was a positive match. It was a tough loss, of course, but I'm happy with the way I was playing today. 

"I was playing better, feeling better on the court physically. I spent a lot of mental energy to focus, to stay there as it was tough at the end. But I'm happy with what I have done."

Ninth seed Sinner was taken the distance by Coric before completing a 6-3 2-6 6-3 victory to advance to the second round. 

Sinner took a medical timeout in the second set while he dealt with some apparent abdominal pain, but he was able to battle back and take the win. 

Diego Schwartzman needed over three hours to come from behind and defeat Karen Khachanov 6-7 (5-7) 6-3 6-3, while his fellow Argentine Federico Delbonis set up a clash with second seed Alexander Zverev by besting Jaume Munar 6-4 3-6 6-4. 

Reigning champion Stefanos Tsitsipas faces a meeting with Fabio Fognini in the second round after the Italian overcame Arthur Rinderknech 7-5 4-6 6-3.  

There were also wins for Hubert Hurkacz, Pablo Carreno Busta, Marin Cilic, Alex de Minaur, Albert Ramos-Vinolas and Sebastian Korda. 

Casper Ruud set up a semi-final with Francisco Cerundolo at the Miami Masters after he defeated Alexander Zverev 6-3 1-6 6-3 on Wednesday.

Ruud's heavy topspin game gave Zverev problems initially, contributing to a 94 per cent success rate from points on his first serve, while Zverev struggled to find rhythm on serve at 58 per cent.

Saving two break points in the opening game of the second seemed to spark Zverev into life, but Ruud was able to regroup and continue dominating from the baseline in the third to comfortably see his way through.

"It was great to get that break early on [in the third set] and I was able to keep it all the way out," Ruud said post-match. "I was serving well. I can thank my serving for the win today."

The Norweigian world number eight lost his first three ATP 1000 quarter-finals on hard court, but played with confidence on the back of a 75 per cent first-serve rate.

He will face Cerundolo, who also advanced into the semi-finals on Wednesday, after Jannik Sinner was forced to retire due to foot blisters. The Argentine was leading 4-1 in the first set after 23 minutes when Sinner called the match.

The world number 103 held a 0-2 record on hard courts prior to this week, but has now made his first ATP 1000 semi-final in as many attempts after progressing past Tallon Griekspoor, Reilly Opelka, Gael Monfils and Frances Tiafoe.

Cerundolo has enjoyed a strong start to 2022, with respective quarter-final and semi-final appearances on clay in Buenos Aires and Rio de Janeiro.

The winner of the upcoming semi-final will make their first ATP 1000 final appearance, while Ruud was able to beat Zverev at third time of asking, losing the opening two games head-to-head.

Emerging Spanish star Carlos Alcaraz continued his rise with a 7-5 6-3 upset of third seed Stefanos Tsitsipas to reach the Miami Masters quarter-finals on Tuesday.

The 18-year-old, who reached last year's US Open final eight after beating Tsitsipas in the third round, proved too good again for the Greek in one hour and 50 minutes.

Alcaraz reached last week's Indian Wells semi-finals and is now 15-2 on the season, with the win setting up a clash with Serbian Miomir Kecmanovic who upset last week's Indian Wells champion Taylor Fritz 3-6 6-1 6-4.

Tsitsipas broke the Spaniard in the sixth game and led 5-2 before Alcaraz reeled off seven straight games to sensationally take the first set.

Alcaraz surged ahead in the second set, with his defence and speed leaving Tsitsipas short on answers.

The Spaniard, who saved seven of eight break points throughout the match, converted his fourth match point for victory.

"It was really, really tough. He was playing unbelievable," Alcaraz said after the match. "All I can say is I fought until the last ball in the first set [to] come back."

Ninth seed Jannik Sinner won 7-6 (7-3) 6-3 over enigmatic Australian Nick Kyrgios, who had a furious outburst directed at umpire Carlos Bernardes.

The Australian was heard to label Bernardes "an absolute clown" and continued to berate the umpire late in the first set, leading to a code violation and two penalties.

Kyrgios completely lost his cool, demanding to speak to a tournament official before smashing his racquet early in the second set, leading to a game penalty as well.

Sinner will next take on Argentine Francisco Cerundolo after he defeated 28th seed Francis Tiafoe lost 6-7 (2-7) 7-6 (7-3) 6-2.

Top seed Daniil Medvedev made light work of Jenson Brooksby 7-5 6-1 to set up a quarter-final showdown with reigning champion Hubert Hurkacz who won 7-6 (7-3) 6-2 over Lloyd Harris. Medvedev will return to the top of the ATP rankings if he wins their quarter-final.

Second seed Alexander Zverev got past Thanasi Kokkinakis 6-4 6-4 and will meet sixth seed Casper Ruud in the last eight, after the Norwegian won 6-3 6-4 over Briton Cameron Norrie.

Jannik Sinner saved multiple match points for the second straight match on Sunday, advancing to the last-16 at the Miami Masters.

After saving three in his opening match against Emil Ruusuvuoiri, the 20-year-old Italian denied Pablo Carreno Busta five times to eventually win 5-7 7-5 7-5.

A Miami finalist in 2021, the Italian was 5-4 down in the second set before winning 11 consecutive points to force a third frame.

Down a break before breaking-to-love in the third, Sinner was fearless with his ground strokes with the game on the line, moving to 5-0 in deciding sets for 2022.

He will face Nick Kyrgios, who continued his strong start to the year with a 6-2 6-4 win over Fabio Fognini.

Taking only 61 minutes to advance after defeating world number seven Andrey Rublev in straight sets in his opening match, Kyrgios hit 24 winners and only lost eight points on serve.

The Australian wildcard and Sinner were supposed to meet at Indian Wells earlier this year, but the latter had to withdraw due to illness.

Fellow unseeded Australian Thanasi Kokkinakis advanced past Denis Kudla, while Francisco Cerundolo upset Gael Monfils.

In the late result on Sunday, Alexander Zverev was a comfortable 6-2 6-2 winner over Mackenzie McDonald.

The German second seed put McDonald under immediate pressure with his return of service, winning 13 of 22 points on the American's second serve.

Meanwhile, Cameron Norrie and Casper Ruud saw their way through in straight sets.

Fifth seed Andrey Rublev has been eliminated from the Miami Open in the second round in straight sets by wild card world number 102 Nick Kyrgios on Friday.

The enigmatic Australian triumphed 6-3 6-0 in 52 minutes to clinch a third round clash with Italian Fabio Fognini, who won in three sets against Japanese Taro Daniel.

The victory marks Kyrgios' third win over a top 10 opponent in the past two tournaments, having topped both Casper Ruud and Jannik Sinner at Indian Wells earlier this month.

Rublev had won titles in Marseille and Dubai earlier this season but was not allowed to settle by Kyrgios who sent down 10-5 aces and had a first serve percentage of 80 per cent.

"I know that he's a player who relies on a bit of rhythm, so I just tried to keep the points short and sharp, just play aggressive," Kyrgios said after the match.

"I'm just happy with my performance, whether it's 7-6 in the third or something like this, I'm just happy to get through."

Second seed Alexander Zverev was made to work for victory against Croatian Borna Coric, winning 6-4 3-6 6-3 in two hours and one minute.

The win marks the 2018 Miami Open runner-up's first triumph at the event since that run to the final.

Sixth seed Ruud eased past Henri Laaksonen 6-1 6-2, while ninth seed Sinner defeated Emil Ruusuvuori 6-4 3-6 7-6 (10-8) in two hours and 40 minutes.

Several seeds were beaten included 13th seed Diego Schwartzman who went down 4-6 7-6 (7-3) 6-4 to Thanasi Kokkinakis. Seeds Lorenzo Sonego, Grigor Dimitrov, Reilly Opelka and John Isner also exited.

Gael Monfils defeated Oscar Otte 7-6 (11-9) 6-1, Pablo Carreno Busta won 6-3 6-2 over David Goffin and 10th seed Cameron Norrie won 7-6 (7-5) 6-4 over Jack Draper.

Rafael Nadal did it tough against Reilly Opelka on Wednesday, eventually winning his way through to the quarter-finals at the Indian Wells Masters.

Nadal displayed an abundance of tactical nous, nullifying the American’s big hitting and service game to emerge the 7-6(6-3) 7-6(7-5) winner.

Along with a 76 percent first-serve rate, Opelka hit more winners with 26 for the match, but the 35-year-old Spaniard was able to grind out points from the baseline with his trademark heavy topspin. As a result, Nadal’s winner/unforced error differential was +14 in comparison to Opelka’s +1.

"He is one of the toughest opponents on tour," Nadal said post-match. "It is very tough to control his weapons with his serve and forehand.

"I think I played my best match of the tournament so far today. I am very pleased with how I was able to win the match, with two difficult tie-breaks. This victory means a lot to me."

The highest ranked player left in the draw, Nadal will now face Nick Kyrgios, who progressed to the quarter-finals after Jannik Sinner withdrew with illness.

Matteo Berrettini made a shock exit, meanwhile, losing 6-3 6-7(5-7) 6-4 to unseeded Serbian Miomir Kecmanovic.

The Italian world number six was put under constant pressure, with Kecmanovic targeting his backhand and hovered the baseline to close the angles on serve.

The 22-year-old’s only other top 10 victory came against Alexander Zverev, also the world number six then, at Cincinnati in 2019. He will now face Taylor Fritz, who defeated Alex de Minaur 3-6 6-4 7-6(7-5).

Also on Wednesday, Grigor Dimitrov edged past John Isner 6-3 7-6(8-6). In his unique style, the Bulgarian 33rd seed came up with the shot of the day, flicking a forehand pass across the visibly stunned Isner.

He will face Andrey Rublev, who defeated Hurbert Hurkacz 7-6(7-5) 6-4. In Wednesday’s other results, Carlos Alcaraz Garfia comfortably defeated Gael Monfils 7-5 6-1, while Cameron Norrie accounted for Jenson Brooksby 6-2 6-4.

Novak Djokovic is delighted to be back in competitive action after he booked his spot in the quarter-finals of the Dubai Tennis Championships.

Djokovic, whose decision not to be vaccinated against COVID-19 caused him to be deported from Australia on the eve of the year's first grand slam, eased to a 6-3 6-3 win over Lorenzo Musetti in his first match and made similarly light work of Karen Khachanov on Wednesday.

The world number one has won in Dubai on five occasions, last doing so in 2020, having elected against defending his title last year.

However, the Serbian is looking good to regain the crown in what is his first tournament on the ATP Tour in 2022, after he was unable to feature in Melbourne. 

Djokovic needed 98 minutes to see off Khachanov 6-3 7-6 (7-2) and tee up a quarter-final tie against qualifier Jiri Vesely.

"I missed it [playing competitively]. This is my life," Djokovic said, with his previous competitive appearances coming in the Davis Cup Finals in November and December.

"This is what I have known for the past 20 years. Tennis is my love. I enjoy bringing positive energy and memories for people who watch."

It was not all plain sailing for Djokovic, who offered up four break points, but the 34-year-old clawed back three of them.

"I was feeling excited and motivated," added Djokovic, who has progressed to the quarters in Dubai every time he has featured at the tournament.

"But also at the same time I was feeling stressed. Particularly at the moments when I was facing break points. I thought the atmosphere in the stadium was terrific."

Djokovic, who will lose his place at the top of the ATP rankings if Daniil Medvedev triumphs in Acapulco, should have little trouble in sealing a semi-final spot, though Vesely does come into that tie on the back of a surprise 6-2 6-4 win over world number 15 Roberto Bautista Agut, who had triumphed in Doha last week.

Murray falls short of landmark win

Second seed Andrey Rublev came from a set down to defeat Kwon Soon-woo 4-6 6-0 6-3, and will go up against American Mackenzie McDonald for a place in the last four.

There was no such joy for former world number one Andy Murray, however, who fell to Jannik Sinner 7-5 6-2.

"It is a special feeling [to share the court with Murray]," said Sinner, who will next face Hubert Hurkacz, a 6-3 6-2 winner over Alex Molcan.

"He is a legend. Winning three grand slams, many, many tournaments and he has had some unfortunate moments with surgeries. His fighting spirit is incredible.

Murray was chasing a 700th tour-level win of his career but failed to muster a single break opportunity against the Italian, who made it to the quarter-finals in Melbourne last month.

Jannik Sinner saved three match points to avoid a shock defeat to Alejandro Davidovich Fokina in the first round of the Dubai Tennis Championships.

After losing the first set, the world number 10 staved off defeat in a nerve-wracking second-set tie-break.

The fourth seed clung on as Davidovich Fokina saw a trio of opportunities to clinch a shock win go begging, the Spaniard made to pay as his Italian counterpart fought back to prevail 4-6 7-6 (8-6) 6-3.

Sinner, who will next face former world number one Andy Murray, said: "It was a very tough match. I know him, but we've never played against each other.

"It was the first time for both of us and it was a tricky one, saving three match points. On the first one I got lucky because it was out, but not so far [out]."

Second favourite Andrey Rublev won both the singles and doubles titles in Marseille last week and continued his fine form with a 6-4 7-5 win over Daniel Evans that saw the Russian send down 28 winners.

Sixth seed Denis Shapovalov had to recover from a set down to see off Marton Fucsovics, though fifth seed Hubert Hurkacz enjoyed a more routine straight-sets triumph over Alexander Bublik.

Eighth seed Roberto Bautista Agut made relatively light work of Arthur Rinderknech but defending champion and seventh seed Aslan Karatsev was stunned 7-5 6-3 by Mackenzie McDonald.

Karen Khachanov needed a little shy of three hours to beat Alex de Minaur, his dubious reward a second-round clash with Novak Djokovic as the world number one continues his return to the Tour following his controversial Australian Open absence.

Daniil Medvedev and Jannik Sinner have been replaced by Andy Murray and Jo-Wilfried Tsonga in the upcoming Rotterdam Open.

World number two Medvedev lost a thrilling five-set Australian Open final to Rafael Nadal on Sunday and does not feel ready to compete in the Netherlands.

The Russian explained his decision in a statement on Thursday, while Sinner has had to pull out due to COVID-19.

"Unfortunately I will not play in Rotterdam this year," Medvedev said. 

"I just got back from Australia and am not ready to compete. Rotterdam is one of the favourite stops. I look forward to coming back in the future."

Roberto Bautista Agut and Borna Coric had already pulled out of the competition. Tournament director Richard Krajicek has confirmed that Murray and Tsonga, who won the event in 2009 and 2017 respectively, will now take part as wild cards.

Andrey Rublev is the reigning champion in Rotterdam after beating Marton Fucsovics in last year's final.