Alexander Zverev recorded the biggest win on clay of his career as he stunned Rafael Nadal in the quarter-finals of the Madrid Open.

Nadal, a five-time champion at this event, was a break up in the first set of his 15th quarter-final at Caja Magica but lost 6-4 6-4 in an hour and 44 minutes.

Zverev had won the previous two meetings with Nadal, both on indoor hard courts, after losing five consecutive matches against the 20-time major champion including a 6-1 6-1 rout in Monte Carlo in their first clay contest four years ago.

The world number six has five clay-court titles to his name, including this event in 2018, but defeating 13-time French Open champion Nadal on his favourite surface in front of a home crowd ranks among Zverev's finest achievements.

It looked as though Nadal was assuming control when he broke to love to lead 4-2 in the first set, but Zverev responded with a break back at the first time of asking.

The German had spoken of the Madrid courts playing faster than other clay events and the conditions certainly seemed to suit his fearless approach as Nadal struggled to deal with his crosscourt backhand.

He won the next three games to clinch a first set in which he lost just four of 16 points behind his first serve.

While Zverev looked increasingly confident, mixing up his shot depth and frequently coming to the net, Nadal cut an unusually frustrated figure even as he showed customary battling qualities to ward off a break point at 1-1.

However, more powerful hitting from Zverev saw him break to lead 4-2, and although he missed two chances for a double break, he closed out the match with minimal fuss.

"Definitely one of the biggest wins of my career," Zverev, who will face Dominic Thiem in the semi-finals, told Amazon Prime Sport. "Beating Rafa on clay is one of the toughest things to do in our sport."

Rafael Nadal saw off Alexei Popyrin to reach the Madrid Open quarter-finals on a day that saw Daniil Medvedev and Stefanos Tsitsipas suffer surprise defeats.

World number two Nadal, chasing a record-extending sixth title on home soil, advanced 6-3 6-3 in a time of one hour and two minutes on Thursday.

Popyrin, playing in his first last-16 match at a Masters 1000 event, broke Nadal in the sixth game of the opening set but the Spaniard otherwise looked comfortable.

Nadal converted four of his six break points to advance through to the last eight for a 15th time, where Alexander Zverev awaits.

"It was difficult," Nadal said in his on-court interview. "The court today was slippery, it was very fast, very dry conditions. The ball was flying a lot. The beginning was super tough. 

"He was hitting every ball and hitting the spots. I'm happy with the victory. It was an important victory, he came here playing well. Every match is tough."

Zverev, who won the competition in 2018, beat British number one Dan Evans 6-3 7-6 (7-3) to set up a meeting with Nadal

However, second and fourth seeds Medvedev and Tsitsipas saw their participation come to an end at the hands of Cristian Garin and Casper Ruud respectively.

Medvedev, who is still yet to reach the quarters in Madrid, lost the only break of serve in the third game of the opening set but recovered by taking the second set in a tie-break.

Garin dominated the deciding set, the world number 25 breaking Medvedev twice and, after a short delay to fix a broken net, advanced 6-4 6-7 (7-2) 6-1.

Tsitsipas, who held championship point against Nadal in the Barcelona Open final, failed to break Ruud on a single occasion as he fell 7-6 (7-4) 6-4.

Alexander Bublik is next up for Ruud after beating Aslan Karatsev 6-4 6-3, while Matteo Berrettini - 7-6 (7-4) 6-4 winner against Federico Delbonis - will meet Garin.

Also vying for a place in the semi-finals are John Isner and Dominic Thiem, who are set to face off after beating sixth seed Andrey Rublev and Alex de Minaur respectively.

Rafael Nadal cruised to victory over birthday boy Carlos Alcaraz to start his Madrid Open campaign in impressive fashion.

The world number two moved into the last 16 with a 6-1 6-2 victory on Wednesday.

After being knocked out of the Monte Carlo Masters by Andrey Rublev in the last eight, Nadal bounced back to win the Barcelona Open last month and continued his momentum in this round-of-32 clash.

As wildcard Alcaraz turned 18, the spectators sang happy birthday to him but he could not mark the occasion with a famous result against his idol, with Nadal broken just once on his way to a 78-minute victory.

Five-time tournament winner Nadal converted five of his seven break points in a ruthless showing, with Real Madrid greats Iker Casillas and Raul in the crowd to watch him.

Nadal will play Alexei Popyrin, a straight-sets winner against rising star Jannik Sinner, in the next round.

Elsewhere, second seed Daniil Medvedev came from behind to defeat home hope Alejandro Davidovich Fokina 4-6 6-4 6-2. It was his first win in seven ATP Tour matches on clay.

"I am happy with the win," said the Russian.

"The first set wasn't easy and I thought it was going to be where I had another 25 break points and I wouldn't win. 

"I finally played quite well and did well in the third set. Madrid is a little faster than other clay tournaments, so it is better for my game."

The win means Medvedev has an 18-3 record this season and faces Chile's Cristian Garin next.

Medvedev's compatriot Aslan Karatsev beat Diego Schwartzman 2-6 6-4 6-1, having also defeated the French Open semi-finalist at the Australian Open this year.

In-form Karatsev will face Alexander Bublik next after his fourth top-10 win of the year.

Fifth seed Alexander Zverev said he was "clinical" in dispatching Kei Nishikori 6-3 6-2 in just 74 minutes, while fourth seed Stefanos Tsitsipas will play Benoit Paire later on Wednesday.

Dominic Thiem surged to an emphatic victory on his return to the ATP Tour at the Madrid Open.

US Open champion and two-time Madrid Open runner-up Thiem was playing his first match in nearly two months on Tuesday, having taken a break to recharge.

But it did not take him long to get back into the groove, the third seed easing through his second-round match with American qualifier Marcos Giron 6-1 6-3 at the ATP 1000 event.

"I was uncertain how things will be going. The game worked out very well in the past days of practice, but I was always practising on the outside courts which are faster, which are smaller, so I was just not sure how it was going to be in the match," Thiem said.

"But there were some things which I think made [the match] a little bit easier after such a long time, especially the conditions in Madrid, which are great for me.

"Then [I have] amazing memories on this court, where I already played probably some of the best matches of my career. I think that's why things worked out quite well tonight."

Next for Thiem in the last 16 is Alex de Minaur, who was leading 6-2 3-0 when Lloyd Harris retired from their match.

It was a largely strong day for the seeded players in the Spanish capital, home hope and ninth seed Roberto Bautista Agut beating Marco Cecchinato 6-2 6-7 (3-7) 7-5 in a first-round clash.

Andrey Rublev – the sixth seed – came from a set down to beat Tommy Paul 6-7 (5-7) 6-3 6-4 and eighth-seeded Italian Matteo Berrettini joins him in the last 16 after defeating compatriot Fabio Fognini 6-3 6-4.

Jannik Sinner, who is seeded 14th, won in the first round after Guido Pella retired in the second set. However, four seeds did tumble out of the draw.

Felix Auger-Aliassime was thrashed 6-1 6-4 by Casper Ruud in the first round and his Canadian compatriot Denis Shapovalov was beaten 6-4 5-7 6-4 by Alexander Bublik in their second-round encounter.

Miami champion Hubert Hurkacz suffered a second successive second-round exit, the 12th seed defeated 5-7 7-6 (9-7) 6-3 by John Millman in a match that went the distance having lost at the same stage in Monte Carlo.

Carlos Alcaraz, a 17-year-old wildcard, will face Rafael Nadal in the second round of the Madrid Open, with the top seeds set to get their campaigns underway on Tuesday and Wednesday.

Alcaraz, featuring in an ATP Masters 1000 event for just the second time, was in impressive form as he saw off France's Adrian Mannarino 6-4 6-0.

The teenager, who will face Nadal on his 18th birthday on Wednesday, fired 19 winners as he took the initiative against his more experienced opponent and his reward is significant.

He became the tournament's youngest ever match winner, beating the record set by Nadal.

"For me, [to] play against Rafa is a dream come true," Alcaraz said as he readies himself to go up against the 20-time grand slam winner.

"Since I was a kid, I wished to play a match against Rafa and now I will be able to here [on] the Centre Court of La Caja Magica in Madrid. It is a really special match against Rafa."

He told Tennis Channel: "It's the best present for my birthday."

The biggest casualty of the day was 13th seed Grigor Dimitrov, who lost 3-6 6-3 7-6 (7-5) to Lloyd Harris early on, the South African now 4-0 against top-20 opponents this year.

Two qualifiers in Pablo Andujar and Marcos Giron played out a remarkable encounter that lasted three hours and 21 minutes.

The first set alone clocked in at just over an hour and a half, but eventually Giron came through the gruelling clash 6-7 (8-10) 7-6 (7-4) 7-5 to set up a meeting with third seed Dominic Thiem.

Fabio Fognini defeated Carlos Taberner 7-6 (7-4) 2-6 6-3 for the right to face eighth seed and Italian countryman Matteo Berrettini.

Diego Schwartzman, the seventh seed, awaits Aslan Karatsev after he beat Ugo Humbert in straight sets in what was the Russian's debut appearance at the tournament.

Dan Evans and John Isner were among the other players to secure progress on Monday.

Denis Shapovalov relished feeling much better on court as he impressively bounced back from two consecutive defeats to win at the Madrid Open.

The number 11 seed brushed aside the challenge of Dusan Lajovic on Sunday, winning 6-1 6-3 in the first round.

Shapovalov had suffered disappointment on Thursday when he was knocked out in the second round of the Estoril Open, an event where he was the number one seed.

He has not reached the quarter-finals in his previous two ATP Tour events but won 90 per cent of his first-serve points against Lajovic, hitting 21 winners to his opponent's five.

"Just definitely felt a lot better - I felt very good on the court," Shapovalov said after a 63-minute win in which he did not lose serve. 

"I'm just happy to get the first win.

"Not much can change in the span of a couple of days, but Madrid is a place where I have had a lot of success, from back in juniors to making semis here in the Masters [1000 event] and finals of Davis Cup.

"It's just a place where it kind of feels like home to me and I just feel so comfortable." 

Shapovalov will face Alexander Bublik – who saw off Marton Fucsovics in straight sets – in round two.

Tommy Paul, meanwhile, will play Andrey Rublev after defeating Pedro Martinez.

In the only match of the day to go the distance, Australian Alex de Minaur battled back to triumph 4-6 7-5 6-1 against Jaume Munar.

He will play either Lloyd Harris or Grigor Dimitrov, who are scheduled to do battle on Monday.

Nikoloz Basilashvili won a fifth ATP Tour title as he triumphed at the BMW Open on Sunday.

The Georgian completed an impressive week in Munich by beating Jan-Lennard Struff 6-4 7-6 (7-5) to clinch the trophy without dropping a set in his five matches.

The win continued what has been a solid 2021 for Basilashvili, who won the title in Doha in March after defeating Roger Federer in his second match following his return from injury.

After retiring from his opening match in Monte Carlo last month before losing to Jeremy Chardy in Barcelona, the world number 35 had looked in fine form in Munich before battling to victory against Struff in just under 86 minutes.

"It wasn't easy and I was super-tight at the end," said Basilashvili. "It was very difficult. It's never easy playing Jan, he's a very big fighter and serves really well.

"I am super happy. It seems like German conditions suit me. This is my fifth [ATP Tour] title and it will give me confidence for the upcoming tournaments."

At the Estoril Open, Albert Ramos-Vinolas emerged victorious from a marathon final against Cameron Norrie.

The 33-year-old was a set and a break down but rallied to win 4-6 6-3 7-6 (7-3) in two hours and 44 minutes in Portugal.

It was the Spaniard's third Tour title and took him to a 16-5 record on clay this season. He has at least seven more wins on the surface than any other ATP player this season.

Jan-Lennard Struff is through to his first final on the ATP Tour after ending Ilya Ivashka's impressive run at the BMW Open in Munich.

Struff had lost in his previous seven semi-final appearances and it appeared the streak may continue when he quickly fell 3-0 behind against his opponent from Belarus.

However, qualifier Ivashka – who had knocked out top seed Alexander Zverev in the previous round – only managed to win two more games in the remainder of a contest that spanned 87 minutes.

A 6-4 6-1 win for Struff sets up a showdown with Nikoloz Basilashvili, who crushed Casper Ruud 6-1 6-2 to progress through from the other half of the draw.

"I am happy to have reached my first final on home soil in Germany and I will try my best tomorrow," seventh seed Struff said after Saturday's match.

Both Basilashvili and Ruud had completed their quarter-final ties earlier on Saturday, but it was the former who coped better with a quick return to action on the clay court, easing to victory in 71 minutes.

At the Estoril Open, Cameron Norrie moved a step closer to a first ATP title after withstanding a barrage of aces to overcome the big-serving Marin Cilic in two sets.

Norrie managed to save five of the six break-point opportunities on his own serve as he eventually prevailed 7-6 (7-5) 7-5. His only previous experience of a final on the ATP Tour came back in 2019, when he lost to Tennys Sandgren at the ASB Classic in Auckland.

"[Marin] was serving great and it was really tricky to get his first serve back. I am fortunate to get through and I am just happy to be in my second final," the Briton said in his on-court interview.

Albert Ramos-Vinolas is the last player standing in his way, the Spaniard battling back after losing his serve in both sets to beat compatriot Alejandro Davidovich Fokina 6-1 6-4.

Jan-Lennard Struff and Filip Krajinovic had contrasting routes into the BMW Open quarter-finals on Thursday.

Home favourite Struff made it to the last eight of the clay-court tournament for the fourth time in his career with a 7-6 (7-3) 6-7 (0-7) 6-2 triumph over German countryman Dominik Koepfer, who had little to celebrate on his 27th birthday in Munich.

Struff recovered from 4-2 down to take the first set and racked up four straight games to seal the deciding set. He served 11 aces and staved off five break points in a match lasting two hours and 39 minutes.

"I am very, very happy that I turned around the first set," seventh seed Struff said in his on-court interview. 

"I played a not good second-set tie-break. Before [that] the set was okay, but I couldn't lock into his service games that much.

"I am very happy that I broke him I the third set and I am very happy to be through. Dominik is a good guy and a very good player."

Fourth seed Krajinovic stands in the way of Struff and a last-four berth, with the Serbian handed a walkover after last-16 opponent Yannick Hanfmann pulled out with a neck injury.

Nikoloz Basilashvili, seeded fifth, defeated Daniel Elahi Galan 6-4 6-2 to set up a last-eight clash with lucky loser Norbert Gombos, who overcame Federico Coria 6-4 6-1.

At the Estoril Open there was a battle between music collaborators as top seed Denis Shapovalov faced off against Corentin Moutet.

The duo were welcomed onto the court by the track 'Drip', which they released together last year.

On the court, it was Frenchman Moutet who managed to snare an upset victory in a 6-4 2-6 6-4 triumph against the Canadian, to score a second top-20 win of the year.

"It was a very close match," Moutet said. "I'm lucky that I won at the end. A few points decided the winner."

Next up is Albert Ramos-Vinolas, who defeated Pierre-Hugues Herbert 6-2 7-6 (7-3).

Cameron Norrie outlasted wildcard Pedro Martinez 4-6 7-6 (7-1) 7-5 to book a quarter-final against second seed Cristian Garin, who never took to the court as opponent Richard Gasquet withdrew with a left adductor problem.

Two-time BMW Open champion Alexander Zverev is hoping to enjoy further success in Munich after shaking off the rust in his opener on Wednesday.

Zverev has been managing an elbow injury and had only played three times since mid-March, swiftly departing Masters 1000 events in Miami and Monte-Carlo.

But the German is back in familiar territory on home soil and made light work of lucky loser Ricardas Berankis.

Zverev, who won the tournament in 2017 and 2018, needed just 87 minutes to claim a 6-2 6-4 victory.

"I haven't played much tennis the past few weeks, so I know I'll need to improve for the next match," he said.

"I've had success in the past and I feel good here. I've played well in the practice and hopefully I can do better on the match court."

Fellow seeds Casper Ruud and John Millman each also advanced, albeit the latter only when Guido Pella retired after the Argentine won the first set 6-4 and was 2-0 down in the second.

At the Estoril Open, Marin Cilic and Kevin Anderson will face off in an enticing quarter-final.

One-time US Open champion Cilic has a 6-1 career lead over Anderson, who has fallen to 105th in the world.

Cilic came from behind to beat Nuno Borges 6-7 (5-7) 6-4 6-4, while Anderson defeated Roberto Carballes Baena in straight sets.

Defending champion Novak Djokovic has revealed he will not play in the Madrid Open next week.

The world number one on Wednesday announced he will not take his place in the draw at the Caja Magica, where he won the title for a third time two years ago by beating Stefanos Tsitsipas in the final.

Djokovic suffered a shock defeat to Aslan Karatsev in the semi-finals of the Serbia Open on home soil last week and the 18-time grand slam champion will not be adding to his list of honours in Madrid.

He stated: "Sorry that I won’t be able to travel to Madrid this year and meet all my fans.

"It's been two years already, quite a long time. Hope to see you all next year!"

Djokovic has won 12 times and been beaten twice this season, claiming a ninth Australian Open crown in February.

The Madrid Open was not staged last year due to the coronavirus pandemic.

Matteo Berrettini outlasted Aslan Karatsev in an entertaining Serbia Open final on Sunday to win his fourth ATP Tour title.

Karatsev stunned world number one Novak Djokovic on Saturday to reach the final, though the Russian fell just short of claiming another scalp as he slipped to a 6-1 3-6 7-6 (7-0) defeat to Berrettini.

Second seed Berrettini could not take a first championship point in a third set that went the distance, but he held his nerve to add to his previous title triumphs at the Swiss Open, Hungarian Open and Stuttgart Open.

Berrettini held serve throughout the first set and broke his opponent in the fourth and sixth games to grab an early foothold in the contest.

But Karatsev, 18 places below world number 10 Berrettini in the ATP rankings, hit back in the second set to pave the way for a tense decider in Belgrade.

The big-hitting pair, competing against each other for the first time on the tour, managed a break of serve each before Italian Berrettini had match point in a gruelling 12th game.

While Berrettini was denied by Karatsev on that occasion, the 25-year-old powered through the tie-break to complete his impressive return to form.

"This title is for my family. This is the first time that they are actually here to see me win the trophy even though it's my fourth one," Berrettini said in his on-court interview.

"This is a special one. We came a long way since I was a kid and they were bringing me everywhere, so I think they deserve to see this kind of tennis and this kind of level. I really love them.

"It's been a pleasure being here. I came here not with the best feelings. I came back from an injury and it's never easy to come back and play this kind of level, this kind of tennis."

Rafael Nadal won the Barcelona Open for the 12th time after saving a championship point in a to end Stefanos Tsitsipas' perfect record on clay this year in a thrilling final.

World number three Nadal, playing just his third tournament of the year, is gearing up for a tilt at a record-extending 14th French Open title.

By defeating the man who landed the Monte Carlo Masters title last week, Nadal showed he is moving through the gears on his favourite surface before heading to Paris.

He won 6-4 6-7 (6-8) 7-5 to maintain his 100 per cent record in finals at this tournament on home soil, but Tsitsipas was left to reflect on a missed opportunity after the 20-time grand slam champion fended off a championship point at 5-4 in the final set.

Nadal trailed 4-2 in the opening set as Tsitsipas signalled he was up for the challenge and brimming with confidence, but back came the 34-year-old to sweep up the next four games.

Tsitsipas broke first in the second set too, inching 2-1 in front, and the Greek looked every bit a warrior capable of living with the best for much of the contest.

It was a rout when these two met in the Barcelona final three years ago, Nadal dropping only three games, but here he needed to work far harder, in what was the 69th clay-court final of his stellar career.

Tsitsipas beat Nadal from two sets down in the Australian Open quarter-finals in February, so dropping the opener here was not cause for panic, but nor was gaining the early break in the second any reason to be confident he would be taking the match to a decider.

Nadal duly broke back but then let two championship points slip by in the 10th game, with Tsitsipas serving. A smash followed by a superb drop volley from Tsitsipas meant the match remained alive.

Tsitsipas could not convert 0-40 on Nadal's serve in the next game, but he won a thrilling tie-break to take the contest all the way.

There was not a solitary break point in the decider until Tsitsipas was a point away from claiming the title in the 10th game, but the King of Clay dug in to hold.

He rubbed salt in the wounds by securing the elusive break in the next game and dropped to the clay in delight after serving it out, ending a pulsating showdown that was finally settled in three hours and 38 minutes.

Aslan Karatsev secured a stunning career-best victory over home favourite Novak Djokovic to set up a Serbia Open final against Matteo Berrettini.

Karatsev showed astonishing defiance to beat the world number one 7-5 4-6 6-4 in the longest ATP Tour match of the year on Saturday.

The third seed from Russia saved 23 of the 28 break points he faced as his aggressive approach paid off, toppling the 18-time grand slam champion in a contest that lasted three hours and 25 minutes.

It was sweet revenge for Karatsev, who was beaten by the legendary Serbian at the semi-final stage of the Australian Open two months ago.

Djokovic had won 11 matches in a row in his homeland, but bowed out despite being 2-0 up in the first two sets as a solitary break in the decider ended his run.

Karatsev, the world number 28, said: "It was a long, tough match [against a] tough opponent.

"You have to put [in] like 200 per cent to beat this guy, it's like playing against a wall. And he also made some good shots.

"He doesn't give you any free points. He always makes you play and you have to be always there because once you miss a couple of shots, he just takes it very quickly. That’s how I lost the second set."

Berrettini secured his place in the final with a 6-1 6-7 (5-7) 6-0 victory over lucky loser Taro Daniel.

Second seed Berrettini only lost six points in the last set after Daniel came from a break down in the second before winning a tie-break to take the second semi-final the distance.

Heading into Sunday's final, Karatsev and Berrettini have never previously faced each other on the ATP Tour.

Rafael Nadal.and Stefanos Tsitsipas will do battle for the Barcelona Open title on Sunday after both cruised into the final in straight sets.

Nadal beat fellow Spaniard Pablo Carreno Busta 6-3 6-2 to stand on the brink of being crowned champion for a 12th time at the Real Club de Tenis Barcelona 1899.

The top seed won 77 per cent of points on his first serve and returned superbly in yet another sublime clay-court exhibition.

Nadal broke Carreno Busta in his compatriot's first service game and ominously charged into a 5-1 lead in imperious fashion on Pista Rafael Nadal.

Carreno Busta broke back to prolong the opening set, but the 20-time grand slam champion wrapped it up in 45 minutes before swiftly taking charge of the second.

The world number three breezed into a 4-0 advantage and did not face a solitary break point as he took just shy of an hour and a half to set up a showdown with Tsitsipas, who knocked him out of the Australian Open at the quarter-final stage in February.

Tsitsipas maintained his magnificent form with a 6-3 6-3 defeat of Jannik Sinner.

The in-form Greek won the Monte Carlo Masters last weekend and matched Andrey Rublev's ATP tour-leading total of 26 victories this season by steering past Sinner.

Second seed Tsitsipas has won all 17 sets he has played on clay this season, having saved all four break points that Sinner earned.