John Millman outlasted Alexei Popyrin in a near three-hour marathon to progress to the second round of the BMW Open.

Eighth seed Millman was made to work exceedingly hard to avoid an early exit, eventually coming through a contest in which the two Australians faced a combined 31 break points by a 7-6 (7-3) 3-6 7-5 scoreline.

Ricardas Berankis won a 22-point tie-break in the first set to defeat Maximilian Marterer, while there were also wins for Millman's next opponent Guido Pella, Federico Coria and Ilya Ivashka.

At the Estoril Open, Kevin Anderson saved a match point at 6-5 down in the second set tie-break and turned around a 4-1 deficit in the third set to beat Frances Tiafoe 4-6 7-6 (8-6) 7-6 (7-4).

"It was obviously a very, very close match," Anderson said. "I think there were a lot of positives, a lot of really high-quality tennis, especially from midway through the second until the end of the match, I was really happy with the way I played.

"I think even if I had lost that match, obviously it's always tough losing, but I definitely felt I took a step in the right direction.

"Getting the win is a big added bonus, it gives me another opportunity to come out in a couple days' time."

Eighth seed Alejandro Davidovich Fokina beat Pablo Andujar in three sets, with Jeremy Chardy and qualifier Nuno Borges also victorious in Portugal.

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.

World number one Novak Djokovic was full of praise for his Serbia Open semi-final conqueror Aslan Karatsev but bemoaned his own "low level" performance.

Karatsev got past Djokovic in the longest match of the 2021 ATP Tour in Belgrade, triumphing 7-5 4-6 6-4 on Saturday.

The match went for three hours and 25 minutes, with the Russian securing a spot in Sunday's final against 10th ranked Matteo Berrettini.

The Serbian had beaten Karatsev in the Australian Open semi-finals two months ago, with the 27-year-old Russian, who is now ranked 28th, returning the favour.

"From my side, I played on quite a low level, in my opinion," Djokovic said.

“[I had] some flashes of good quality tennis. I was fighting. That is a positive.

"I was really trying all the way [and] the crowd was great. They carried me and tried to lift me up, all the way to the end.

"Because of them, I think I won the second set. Unfortunately in the third, he was just the better player in the decisive moments. I had my chances, but that is sport."

Djokovic was gracious in defeat, offering a thumbs up immediately after Karatsev secured victory along with complimentary words to his opponent who saved 23 of 28 break points.

"Karatsev showed a lot of courage and that is why I gave him the thumbs up," Djokovic said.

"I felt like he deserved to win… Once the final point is done, there is never bad blood. We are rivals on the court, but I don’t hate anybody. I can’t be upset with him if he beat me.

"I have to be upset with myself and question why I lost the match. Whoever beats me deserves the credit and I gave him that.

"I lost to a better player who was just more courageous. He went for his shots at the right time and it worked for him."

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 fended off Kei Nishikori to reach the quarter-finals of the Barcelona Open along with the in-form Stefanos Tsitsipas on Thursday.

Top seed Nadal secured an opening-set bagel in just 30 minutes, but Nishikori hit back to force a decider before the 20-time grand slam champion prevailed 6-0 2-6 6-2.

Nishikori hit only three winners as he was blown away in the first set, but broke twice in the second to ensure Nadal was taken to three sets in back-to-back matches for the first time in this tournament – having overcome Ilya Ivashka in the second round.

The world number three saved three break points from 0-40 down in the final set and Nishikori saw another two come and go, with a more clinical Nadal breaking twice to advance.

Nadal will now face unseeded Brit Cameron Norrie, who also won the first set 6-0 and was 5-3 down to David Goffin in the second when the Belgian retired due to a leg injury.

Newly-crowned Monte Carlo Masters champion Tsitsipas defeated Alex de Minaur 7-5 6-3, stretching his straight-sets winning streak to seven matches.

Next up for the second seed is a meeting with Felix Auger-Aliassime, who beat fellow Canadian Denis Shapovalov 6-2 6-3, while Jannik Sinner beat Roberto Bautista Agut 7-6 (11-9) 6-2.

Andrey Rublev, Diego Schwartzman and Pablo Carreno Busta also made it through.

Two seeds fell in the Serbia Open, with Federico Delbonis taking out Dusan Lajovic 6-3 2-6 6-4 and Taro Daniel defeating John Millman 3-6 6-2 6-3.

Gianluca Mager moved into the quarter-finals at the expense of Alexei Popyrin and Aslan Karatsev battled past Aljaz Bedene 6-3 4-6 7-6 (7-5) in Belgrade.

Novak Djokovic thought he was "pretty flawless" in his first match of the Serbia Open, but Rafael Nadal was given a scare in his clash with qualifier Ilya Ivashka at the Barcelona Open.

World number one Djokovic suffered a shock third-round exit to Dan Evans at the Monte Carlo Masters last week but ruthlessly dispatched Kwon Soon-woo 6-1 6-3 in his home city of Belgrade.

Djokovic broke his opponent five times to set up a meeting with eighth seed and fellow Serbian Miomir Kecmanovic, who battled past qualifier Arthur Rinderknech in three sets, in the quarter-finals.

"I thought it was a pretty flawless performance," Djokovic said. "I moved well, I was mixing up the pace quite well, making him play. I served well in the important moments, [and] overall I just felt great."

On playing in front of his family and friends, the two-time Serbia Open champion added: "It gives you an extra push, an extra motivation, energy to really give your best and leave it all out on the court.

"I think also that made me feel comfortable and confident on the court and I played really good. I'm really pleased with the quality of tennis."

Second seed Matteo Berrettini defeated fellow Italian Marco Cecchinato 6-4 6-3 and will face either Filip Krajinovic or Nikola Milojevic in the last eight of the clay-court tournament.

Over in Barcelona, Nadal – an 11-time champion at the event – was out to make a statement after a rare defeat on the dirt to Andrey Rublev in Monte Carlo.

But the 'King of Clay' needed two hours and 20 minutes to fight back against the unheralded Ivashka 3-6 6-2 6-4 to reach the round of 16, where he will face Kei Nishikori. Nadal is now 62-4 at a tournament where he once won 41 straight matches.

Second seed and Monte Carlo champion Stefanos Tsitsipas hammered Jaume Munar 6-0 6-2, while third seed Rublev - runner-up to the Greek on Sunday - joined Pablo Carreno Busta (6) and Alex De Minaur (14) in making it through.

Evans was unable to follow up his run in Monte Carlo with the 16th seed beaten by Corentin Moutet in a lengthy three-setter, while Fabio Fognini (9) was defaulted for unsportsmanlike conduct after verbally abusing a line official when trailing 6-4 4-4 to Spanish qualifier Bernabe Zapata Miralles.

Jannik Sinner set up a clash with Roberto Bautista Agut at the Barcelona Open as he vowed to keep making progress after cracking the top 20 for the first time.

Italian 19-year-old Sinner is a fast-rising new star of the men's game and now has a ranking to match his age. However, he was put in his place by Novak Djokovic last week in Monte Carlo, before the world number one was himself dealt a jolting defeat by Dan Evans.

Sinner sped past Belarusian Egor Gerasimov in the first round in Barcelona on Tuesday, winning 6-3 6-2, and it will be wily world number 11 Bautista Agut who stands in his way of going deeper into the tournament.

In two meetings on hard courts this season, Sinner has edged out 33-year-old Spaniard Bautista Agut in tight deciding sets, and now they face a reunion on clay.

"He lost in Dubai against me, he lost in Miami against me, now we play once more here, so it's quite a small period of time," said Sinner.

"We're playing now our third match already, so it's going to be a very tough match. He is very, very solid. I never played against him on clay. I'm trying to be ready in the best possible way."

Bautista Agut barged past fellow Spanish player Pablo Andujar, scoring a 6-4 6-0 win.

Sinner was proud to enter the ATP top 20 this week but sees it as just a step on his journey, saying: "Obviously it's a good number, but for me at the moment not that important."

He added, quoted on the ATP website: "[I'm] just trying to improve day after day with my team and trying to improve as a player and the ranking is what it is. I'm happy to be top 20 player but the road is long so a lot of work to do."

Albert Ramos-Vinolas, Lorenzo Musetti and Frances Tiafoe, who fought off 17-year-old Spanish prospect Carlos Alcaraz, were also among Tuesday's winners in Barcelona.

Star turn Djokovic begins his campaign at the Serbia Open on Wednesday when he tackles Kwon Soon-woo, with the 18-time grand slam winner having received a first-round bye.

Tuesday's play in Belgrade saw wins for, among others, Federico Delbonis, Aljaz Bedene and Miomir Kecmanovic.

Kei Nishikori's comeback surprised the former world number four, who survived a major scare to advance at the Barcelona Open.

Nishikori trailed 6-4 4-2 and was forced to break serve as Guido Pella attempted to close out the match in the second set, before sensationally rallying to a 4-6 7-6 (7-4) 6-2 win on Monday.

A two-time champion at the ATP 500 tournament on the Barcelona clay, Nishikori broke serve on three occasions in the final set en route to the second round.

"He had the match today at 6-5, serving [for the match]," said Nishikori. "He was much better in the first and second [sets] and 3-0 up in the tie-break. I don't know how I fought through. [In the] third set, I was playing much better.

"I was making so many unforced errors in the first and second [sets]. Maybe he got a little bit tired and I was playing strong in the third set. I want to take that to the next round… The way I fought today and the way I played in the third set was good."

Next up for 2014 US Open finalist Nishikori is 13th seed Cristian Garin.

Ilya Ivashka topped Tallon Griekspoor 6-3 6-1 and the qualifier's reward is a showdown with top seed and 20-time grand slam champion Rafael Nadal.

Cameron Norrie, Pablo Andujar, Jeremy Chardy, Pierre-Hugues Herbert, Jaume Munar, Federico Gaio, Egor Gerasimov and Bernabe Zapata Miralles all advanced to the last 32.

At the Serbia Open, seeds Filip Krajinovic and John Millman booked their spots in the round of 16.

With the ATP 250 tournament being staged for the first time since 2012 and headlined by world number one Novak Djokovic, Serbian fifth seed Krajinovic overcame Stefano Travaglia 7-5 5-7 6-3 in a Belgrade rollercoaster.

Millman – the Australian seventh seed – took down local wildcard Danilo Petrovic 7-5 6-4 as Marco Cecchinato and Nikola Milojevic won through.

Roger Federer has confirmed he will grace the clay courts at the French Open and Geneva Open.

The 20-time grand slam champion made his comeback at the Qatar Open last month after a long absence following knee surgery.

Federer was beaten by Nikoloz Basilashvili at the quarter-final stage in Doha before opting against playing in Dubai and Miami.

The 39-year-old Swiss on Sunday announced he will feature on home soil in a Geneva Open event that gets under way on May 16.

World number seven Federer will also be in the draw for the second grand slam of the year at Roland Garros, where he reached the semi-final two years ago in his first appearance at the Paris major since 2015.

He tweeted: "Hi everyone! Happy to let you know that I will play Geneva and Paris.

"Until then, I will use the time to train. Can't wait to play in Switzerland again."

Rafael Nadal will be a strong favourite to surpass Federer's tally of grand slam titles in Paris, where he has won the French Open a record 13 times.

Stefanos Tsitsipas landed the first Masters 1000 title of his career as he scored a thumping 6-3 6-3 win over Andrey Rublev in Monte Carlo.

The Greek star had lost his previous two finals at this level, with Rafael Nadal denying him in Toronto and Novak Djokovic beating him in Madrid.

However, he had the measure of Russian Rublev on the Monte Carlo clay on Sunday, breaking his opponent's serve three times and giving away nothing on his own delivery.

Tsitsipas, who lives in Monte Carlo, said he had experienced an "unbelievable week", declaring it was the pinnacle of his career to date.

"I can't describe the feelings right now," he said on Amazon Prime. "I'm overwhelmed by so many different emotions.

"It's incredible I'm able to be in the position I am, and I think we both deserved being in the final and put on an amazing fight and an amazing show.

"Generally I would consider it the week of my life so far. I knew he was going to be a very difficult opponent to face and there were a lot of nerves coming into that match.

"I've played him in the past, he always wants to bring the best out of us when facing each other."

Rublev beat 11-time Monte Carlo champion Nadal in the quarter-finals, but the 23-year-old could not hit the heights of that performance in the title match.

Tsitsipas, 22, said: "I'm just proud of the way I managed to behave and to be out on the court today.

"The clay-court season couldn't start better and it's the best thing right now, winning my first Masters 1000, and it's even more special doing it here on home soil in Monte Carlo and doing it on clay which is my favourite surface."

Andrey Rublev reflected on an "amazing feeling" as he booked a Monte Carlo Masters final appearance against Stefanos Tsitsipas.

The Russian has had a remarkable week at the Masters 1000 event that included a stunning win over 11-time champion Rafael Nadal in the quarter-finals.

Rublev continued his fine run with a 6-3 7-5 win over Casper Ruud on Saturday to ensure he will do battle against Tsitsipas in his first final at this level.

Tsitsipas comfortably saw off Dan Evans – who had beaten Novak Djokovic earlier in the tournament – winning his semi-final 6-2 6-1.

Rublev had 21 winners in his 80-minute victory over Ruud and has a record of 24-4 this season, the ATP Tour's best.

"It is an amazing feeling - it is my first [Masters] final, so I am really happy," said Rublev. 

"We will see what is going to happen [in the final]. I will try to do my best.

"Casper is a really amazing player, especially on clay. Since the beginning he put a really high intensity [on the court] and was really tough. 

"I knew that I needed to raise my level if I wanted to fight against him, because if I [did] not raise the level I [would] lose for sure."

Rublev defeated Tsitsipas in straight sets on his way to winning an ATP 500 title in Rotterdam last month.

Six of his eight ATP titles have come since the start of last year.

It took Tsitsipas, who has not won a tournament for 14 months, only one hour and nine minutes to see off the challenge of Evans, forcing 11 break points to the Briton's one.

"I am indeed pleased with the performance," Tsitsipas said, with the Greek yet to drop a set in Monte Carlo.

"I found ways to play at my best. It was really difficult to maintain my level of consistency and I am really happy I managed to deal with all the different moments during the match.

"I'm feeling good. I'm feeling energised. I still have plenty of gas and energy left in me. I was able to have all of my matches done in two sets, so that is a big plus. 

"I am happy to be able to play that way, just take it match by match, approach each individual match with the same intensity and energy - I'm really focused for Sunday."

Rublev has won three of his six career meetings with Tsitsipas and one of their two battles on clay.

Tsitsipas will be competing in his third Masters final, having lost to Nadal and Djokovic in his two previous appearances, the last of which came two years ago in Madrid.

Overall, Tsitsipas has won just five of his 13 ATP finals.

Rafael Nadal was dumped out of the Monte Carlo Masters as Andrey Rublev completed a superb 6-2 4-6 6-2 victory in their quarter-final clash.

Nadal went into the meeting with a 73-5 record at the event but Russian Rublev was in inspired form to stun his Spanish opponent.

The 11-time champion looked set to complete a trademark comeback after taking a 74-minute second set, yet Rublev held firm in the decider to claim a memorable victory after two hours and 33 minutes on court.

"I cannot imagine being in the situation of Rafa, knowing that you are the best player on clay and you have that pressure every time," Rublev said, according to the ATP Tour website.

"I think for him it must be incredibly tough every time. I am in shock [with] the way he is playing under this pressure and that is why he is a legend."

Rublev will face Casper Ruud in Saturday's semi-final after he overcame defending champion Fabio Fognini 6-4 6-3.

Dan Evans followed up his superb victory over Novak Djokovic on Thursday with a slender win over David Goffin to reach his first Masters 1000 semi-final.

World number 33 Evans, who had come into the tournament having lost his previous 10 matches on clay, overcame Goffin 5-7 6-3 6-4 in two hours and 42 minutes.

"I am proud of how I came back today, especially with what happened in the first set," he said after the match.

"I felt my concentration wasn't great and I am really happy with coming through. Yesterday would not have been worth it with a bad performance today."

Evans will face Stefanos Tsitsipas, who progressed when opponent Alejandro Davidovich Fokina retired injured in their quarter-final.

Spaniard Davidovich Fokina did not return for the second set after earlier receiving treatment during the first, which Tsitsipas won 7-5.

Novak Djokovic admitted he played an "awful" match against Dan Evans at the Monte Carlo Masters as Rafael Nadal advanced with ease to the quarter-finals.

World number one Djokovic, playing in his first tournament since winning a ninth Australian Open in February, suffered his first defeat of 2021 on Thursday.

Evans, who had never before reached the last eight of a Masters 1000 tournament, won 6-4 7-5 with a performance that belied his relative lack of success on clay.

The 30-year-old Briton will now meet David Goffin, who surprised fifth seed Alexander Zverev 6-4 7-6 (9-7).

"To be honest, this has been probably one of the worst matches and performances from my side I can recall in the last years," said Djokovic. "I don't want to take anything away from his win, but from my side, I just felt awful on the court overall. Just nothing worked. It's one of those days."

Saying he felt "completely the opposite" to Wednesday's win over Jannik Sinner, Djokovic added: "Just was obviously very, very windy, tough to play in these kinds of conditions against a guy like Evans who makes you move. He's very unpredictable with his shots. He dismantled my game."

Eleven-time Monte Carlo champion Nadal had no such problems in his match as he dismissed Grigor Dimitrov 6-1 6-1 in 55 minutes.

Nadal, who boasts a 14-1 career record against the Bulgarian, did not face a break point in either set against his off-colour opponent.

Dimitrov started the match with three double faults in his opening service game and was 4-0 down in each set.

"[I am] sorry for him. He played a bad match. That is the truth," said Spaniard Nadal. "He made a lot of mistakes. I was there. I was doing the right thing, but it is true that today was more his fault than my good tennis."

Nadal will face Andrey Rublev after the Russian battled past Roberto Bautista-Agut 7-6 (7-2) 5-7 6-3.

Stefanos Tsitsipas, who beat Cristian Garin 6-3 6-4, will face Alejandro Davidovich Fokina next, while Fabio Fognini's straight-sets win over Filip Krajinovic set up a meeting with Casper Ruud.

Dan Evans produced a stunning victory over Novak Djokovic at the Monte Carlo Masters, revealing the world number one had irritated him before the match even began.

A 6-4 7-5 victory for 33rd-ranked Evans in his first career clash with Djokovic carried the Briton through to his first Masters 1000 quarter-final and inflicted a first defeat of 2021 on his opponent.

The seeds of the upset were planted before the players hit the court, Evans later revealed, with the 30-year-old having been irked at having to wait for Djokovic in the locker room.

Top seed Djokovic was playing his first tournament since winning the Australian Open in February, for his 18th grand slam title, and he found it tough against a player who has previously enjoyed little success on clay.

"I thought I did a good job to get out of my service games. He had so many break points but didn't take them, so I was a little lucky there," Evans told Amazon Prime.

"I ran around the first second serve I got, to tell him I'm not going to just stand back and rally, I'm going to try to hit his second serve a little, and I got a few doubles out there."

Djokovic served four double faults, with Evans setting the tone for the match by surging 3-0 ahead early in the opening set.

"He kept me waiting at the start of the match in the changing rooms a little bit, so it was a little annoying," Evans said. "I was ready to go from that, so that got me a little extra fired up."

Rather than being intimidated by the presence of Djokovic on the other side of the net, Evans indicated he treated the Serbian like just another opponent, there to be beaten.

"That's why we roll the balls out, it's one against one and we've got to see who wins," Evans said.

"He gave me some cheap ones today which he never normally does, so I was a little lucky there, but I'm just really happy with coming through."

Evans' win was hailed by former British number one Tim Henman, who said: "He played fantastic tennis. In difficult conditions, he was the one that really dealt with it so well.

"Those first three games where he got up a double break, that probably changed his mindset. It increased his belief and Djokovic was frustrated, but in so many critical moments it was Evans who came up with the great tennis.

"It's an unbelievable achievement. Evans has won so few matches on clay so to beat the world number one, it's an amazing win."