Daniil Medvedev ended his wait for a first win over Roberto Bautista Agut at the Halle Open as his impressive start to the grass-court season continued.

The world number one, who reached the final at 's-Hertogenbosch last week only to suffer a shock defeat to Tim van Rijthoven, had not beaten Bautista Agut in three previous matches.

But his duck against the Spaniard is over following a 6-2 6-4 win, which set up a semi-final meeting with Oscar Otte after the German saw off Karen Khachanov in three sets.

"I remember all the matches we had… He was playing some [great] tennis and it was tough for me to win," Medvedev said of his previous meetings with Bautista Agut. 

"Today I had my plan, managed to keep it going. Definitely got more edge on the most important points, because he had more break points than me. It was not easy, and I'm happy to win."

Hubert Hurkacz, a Wimbledon semi-finalist last year, is also into the last four after edging Felix Auger-Aliassime in two tie-breaks and will face Nick Kyrgios, who beat Paulo Carreno Busta in straight sets.

Elsewhere, Matteo Berrettini was victorious at the Stuttgart Open and is on course to go back-to-back at the Queen's Club Championships after seeing off Tommy Paul 6-4 6-2 to progress to the semi-finals.

Botic van de Zandschlup is his next opponent, the Dutchman overcoming Alejandro Davidovich Fokina 6-2 6-4.

Meanwhile, Filip Krajinovic had to come from a set down to end Briton Ryan Peniston's run at the quarter-final stage, with his reward a meeting with former US Open champion Marin Cilic, a straight-sets victor over Emil Ruusuvori.

World number one Daniil Medvedev is through to the quarter-finals of the Halle Open after beating Ilya Ivashka in a routine straight-sets win.   Medvedev only played and defeated the Belarusian six days ago at the Rosmalen Grass Court Championships, and triumphed again as he came through in Germany 7-6 (7-4) 6-3.   After saving three set points to stay in the opening set, Medvedev sealed it on a tie-break, before easing through in the second.   "He is a great player," Medvedev said of Ivashka after the win. "He had a lot of bad luck with injuries at the beginning of the season. At the end of last season he was playing really great tennis.   "I've known him since I was very young, we actually played in Futures, Challengers, and on the ATP Tour. He beat me once in the Davis Cup, which is a really important tournament. So he knows how to play tennis, he knows how to play well on grass, so I'm really happy that two times in a row I managed to pass a tough test."   He will now play seventh seed Roberto Bautista Agut in the last eight after the Spaniard beat Tallon Griekspoor 6-7 (6-8) 6-4 6-2.   Eighth seed Karen Khachanov is also through after defeating Serbian Laslo Djere 7-6 (7-4) 6-4, and will face Oscar Otte after the German overcame Nikoloz Basilashvili 4-6 6-0 7-6 (7-3).

At the Queen's Club Championships, second seed Matteo Berrettini came from a set down to finally see off Denis Kudla, winning 3-6 7-6 (7-5) 6-4.

Defending champion Berrettini was troubled by the world number 82, and was just a tie-break away from suffering an upset, but the Italian came through as he belted down 22 aces in the match.

Berrettini faces Tommy Paul in the quarter-finals after the American beat Stanislas Wawrinka in straight sets, 6-4 6-1.

Ryan Peniston carried on from knocking out number one seed Casper Ruud by beating Francisco Cerundolo 6-0 4-6 6-4, setting up a last eight clash with Filip Krajinovic after he came from behind to defeat Sam Querrey 4-6 6-3 6-4.

Top seed Casper Ruud suffered a shock first-round exit at the Queen's Club Championships, going down in straight sets to British ATP Tour debutant Ryan Peniston in west London.

The French Open runner-up struggled to get going as he fell to a 7-6 (7-4) 7-6 (7-2) defeat to the world number 180, who was backed by a boisterous home crowd throughout.

Ruud struggled from the off as Peniston forced four break points in the Norwegian's first service game, and his miserable outing was rounded off when his opponent raced into a 5-1 lead before serving out a second-set tie-break.

After claiming the scalp of the world number five, Peniston told the BBC: "I can't really believe it. It feels like a dream. It doesn't feel real.

"I think I've been playing well. Casper is an unreal player and he did so well at the French Open, so I knew it was a tough ask. Four or five years ago I was sitting in the crowd just watching so to be here now is just unreal."

Ruud was not the only big name to fall at the first hurdle, with fifth seed Diego Schwartzman going down 6-1 6-4 against big-serving Sam Querrey to become the fourth of the top five seeds to fail to reach the round of 16.

Second seed and defending champion Matteo Berrettini is the exception after faring much better against another home favourite, cruising past Dan Evans 6-3 6-3, while Stan Wawrinka downed Francis Tiafoe 7-6 (7-2) 6-7 (6-8) 7-6 (7-5), and Denis Shapovalov's clash with Tommy Paul was suspended by darkness at one set apiece. 

Elsewhere, world number six Stefanos Tsitsipas progressed through his opening match at the Halle Open, beating Benjamin Bonzi 7-6 (7-1) 1-6 6-3 to set up an enticing last-16 clash with Nick Kyrgios, who bested Daniel Altmaier 6-3 7-5.

Fourth seed Felix Auger-Aliassime also progressed after being taken to three sets, beating Marcos Giron 6-3 5-7 6-3.

Meanwhile, defending champion Ugo Humbert will face a tough round-of-16 match against fifth seed Hubert Hurkacz after the Pole overcame Maxime Cressy 6-4 4-6 6-4. 

Matteo Berrettini secured his sixth ATP Tour title with a 6-4 5-7 6-3 victory over Andy Murray at the Stuttgart Open.

Berrettini, playing in his first tournament since injury, raced out the blocks to break Murray in just his second service game, before the Scot failed to capitalise on four break points in the following game.

A similar pattern continued for the remainder of the first set, with neither player able to capitalise on break-point opportunities before Berrettini claimed the 1-0 lead with a booming forehand down the line.

That was the first set that Murray had lost in the tournament and he responded by producing a gritty performance in the second.

Berrettini squandered three chances to break at 4-4 before a double fault in the tie-break handed Murray three set points, and the three-time grand slam champion duly obliged to level.

The Italian opened the decider with a break, with Murray requiring a medical timeout for a leg injury, and the world number 10 claimed victory after his opponent had required more treatment.

Berrettini added a second Stuttgart crown to his name, having lifted the title in 2019, while it was his third grass-court success.

The 26-year-old will look to carry that form into Wimbledon, which starts on June 27, while the injury will be of concern to Murray, who was denied his first title since 2019.

Nick Kyrgios said he was racially abused by a spectator during his semi-final with Andy Murray at the Stuttgart Open on Saturday.

Murray won the match 7-6 (7-5) 6-2 to advance to the final, where he will play Matteo Berrettini on Sunday.

However, Kyrgios had greater concerns as he took to Instagram afterwards to say he was called a "little black sheep" by someone in attendance.

"When is this going to stop? Dealing with racial slurs from the crowd?" he wrote.

"I understand that my behaviour isn't the best all the time – but 'you little black sheep', 'shut up and play' – little comments like this are not acceptable. When I retaliate to the crowd, I get penalised. This is messed up."

Meanwhile, Murray's win saw him reach his first tour-level final on grass since 2016.

The three-time major winner upset Stefanos Tsitsipas in the previous round – his first win over a top-five opponent in six years – and followed that up against Kyrgios with another impressive performance.

"A lot of ups and downs, but I kept going and kept working and finally managed to get to another one. I am proud of the effort I have put in," Murray said after securing the win.

He moves up to 47th in the live ATP rankings – the first time he has been in the top 50 since May 2018 – and his clash with Berrettini will be his 70th career final.

"You're always battling yourself as well as the opponent, it's one of the difficult things about individual sports," he added in relation to Kyrgios' frustrations during the game.

"Nick has the potential to be one of the best players in the world, there's absolutely no question about that. But he obviously got very frustrated in the second set and made it a lot easier for me.

"I'm happy to be in the final. I've played well this week and I've got a great opportunity against Matteo tomorrow."

Andy Murray reached his first tour-level final on grass since 2016 with a straight-sets victory over Nick Kyrgios at the Stuttgart Open on Saturday.

The three-time major winner stunned Stefanos Tsitsipas in the previous round – his first win over a top-five opponent in six years – and followed that up with another fine victory.

Murray, who last contested a final on grass when winning Wimbledon for a second time, prevailed 7-6 (7-5) 6-2 against Kyrgios.

He moves up to 47th in the live ATP rankings – the first time he has been in the top 50 since May 2018 – and will face Matteo Berrettini in what will be his 70th career final.

Aiming to keep alive his hopes of a ninth career title on grass, Murray saved both break points faced in the first set and showed good resolve to edge Kyrgios in the tie-break.

The second set was not as tightly contested, with the 35-year-old showing few signs of fatigue as he twice broke Kyrgios' serve to reach Sunday's final in Germany.

Berrettini had earlier defeated Oscar Otte 7-6 (9-7) 7-6 (7-5) to reach his first tour-level final of an injury-hit season.

The world number 10 fired 18 aces en route to overcoming home favourite Otte in a time of one hour and 48 minutes.

"I am really happy," Berrettini said in his on-court interview. "Arriving at the tournament, that was the goal [to reach the final].

"From thinking about it and actually making it is a big difference. I am happy I am here and have another chance to play another final after months without playing.

"This means this is my level and I have proved once again I am comfortable at this level and on this surface. I really like it here at Stuttgart."

Matteo Berrettini made a winning return in his first match back since hand surgery after defeating Radu Albot at the Stuttgart Open.

The world number 10 was forced to sit out the ATP clay season after undergoing surgery following his withdrawal from Miami.

But the Italian was in fine form upon his return as he saw off Moldovan qualifier Albot with a battling 6-2 4-6 6-3 victory to get his grass-court season underway.

Following his last-four appearance at the Australian Open, Berrettini will be seeking another deep run at Wimbledon this year, after reaching his maiden grand slam final there last summer.

The former world number six will have to wait to discover his quarter-final opponent however, after rain forced a suspension in the match between Lorenzo Sonego and Jan-Lennard Struff. 

Sonego took the opening set in a tie break, with the match to be finished on Thursday.

At the Rosmalen Grass Court Championships, Jenson Brooksby likewise saw his match against Hugo Gaston brought to a standstill by overhead conditions, with the American leading 4-2 in the first set.

Matteo Berrettini has confirmed he will skip the French Open later this month as he continues to recover from surgery on his right hand.

The Italian has played only six matches since his semi-final loss to Rafael Nadal at the Australian Open in January, undergoing surgery following the Indian Wells Masters.

On Saturday, the 26-year-old confirmed he is making progress but not yet ready to return for the second grand slam of the year.

"My hand is feeling great, and I am working hard to build up my match fitness," Berrettini posted on Instagram.

"My team and I have made the decision that going straight back into five-set matches on clay at Roland Garros would not be sensible, therefore I will delay my comeback to compete in the full grass season.

"Thank you as always for all the support. I can't wait to be back competing."

The world number eight reached the quarter-finals last year in Paris, losing to eventual champion Novak Djokovic in four sets, before losing again in four sets to Djokovic in the Wimbledon final.

Matteo Berrettini could miss the French Open after the world number six was forced to withdraw from three tournaments as he continues to recover from minor hand surgery.

The Italian progressed to the Wimbledon final in 2021 and started the new season in encouraging fashion as he reached the Australian Open semi-finals, where he was well-beaten by eventual winner Rafael Nadal.

However, the 25-year-old has seemingly struggled from then on, with his next best performance coming in Rio – where he made the last eight – as he limped to a 9-6 record so far in 2022.

Further difficulties followed for Berrettini after he sustained an injury to his right hand late in March, forcing him to withdraw from the Miami Open before undergoing a "minor operation".

Berrettini provided another update on Instagram on Thursday, revealing he would not feature at the Monte-Carlo Masters, scheduled to start later this week, or the Madrid Open and Italian Open at the start of May.

The latter tournament in Rome begins just two weeks before the second grand slam of the year, leading to concerns that Berrettini may not feature at Roland Garros.

"UPDATE – following advice from the medical experts, my team and I have decided that it is crucial I do not put time pressure on my recovery process," he posted.

"We have therefore decided I should withdraw from the Monte-Carlo, Madrid and Rome tournaments to ensure I give myself the proper amount of time to return at my highest level.

"Withdrawing from these events, particularly Rome, was an extremely tough decision, however it is the right one to ensure many more years of competing at the highest level for the biggest trophies.

"Thanks very much for all the support. My recovery process is on track and I look forward to seeing you on-court soon."

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.

Matteo Berrettini survived a scare to eventually progress to the fourth round at the Indian Wells Masters on Tuesday.

The Italian sixth seed had to fight from 2-5 down in the second set and saved three set points, before powering through to triumph 6-4 7-5 over Lloyd Harris.

"I got a little bit nervous," Berrettini said post-match. “I didn’t like how I handled the start of the second set. I let the anger get out a little bit, which helped. I found the right balance in order to break him in the important moment and then I had the momentum.”

The world number six found another level in reeling off five straight games, and will now face unseeded Miomir Kecmanovic, who accounted for Botic van de Zandschulp 7-6(6-3) 7-5.

Taylor Fritz was also pushed by Spanish qualifier Jaume Munar, taking a third-set tiebreaker to progress to the fourth round.

The 20th-seeded was made to work for it in a match that lasted just under three hours, but Munar feel short in the clutch, with two unforced forehand errors in the closing tiebreak to give Fritz a three-point gap.

In Tuesday's last game, Andrey Rublev showed rare composure to progress past Frances Tiafoe 6-3 6-4. 

Neither got off to the best of starts, with Rublev and Tiafoe sharing service breaks in the opening four games of the first set. The characteristically volatile Rublev managed to regroup, though, and stayed calm even when Tiafoe got his home crowd on side. 

Despite a low 67 percent on first serve, Rublev won 83 percent of those points, while Tiafoe did himself no favours with an even lower 58 percent first-serve rate.

Last-year’s semi-finalist will face 29th-seeded Alex de Minaur, who defeated Tommy Paul 7-6(6-2) 6-4.

The Australian world no. 31 faced immediate difficulty on service, with only his second service game going to eight consecutive deuces, after five saved break points. He eventually saw the match through, after breaking for 4-3 in the second set.

Fellow seeds Hubert Hurkacz and Grigor Dimitrov both went through relatively unscathed, with respective wins over Steve Johnson and Alexander Bublik.

Dimitrov will face John Isner, who saw past Diego Schwartzman 7-5 6-3 in Tuesday’s other result.

Third seed Alexander Zverev has been knocked out of the Indian Wells Masters by Tommy Paul in his first game since his expulsion from last month's Mexican Open for unsportsmanlike conduct.

Unseeded American Paul triumphed over the German 6-2 4-6 7-6 (7-2) in two hours and 17 minutes, rallying back from a break down in the final set.

Paul hit less winners, 26-21 to Zverev but made less unforced errors 25-19, while his serve and volley game was a key feature.

"I played a really high level today," Paul said during his on-court post-game interview. "The last time I played him, I played well, I put pressure on him so I knew how i wanted to play so I came out and executed him well.

"I played well when it came down to the breaker, so I'm pretty happy with my performance."

Zverev had not played since being expelled in Acapulco after a stunning outburst where he struck his racquet on the umpire chair several times after a doubles defeat.

Ninth seed Felix Auger-Aliassime was a major casualty, going down to Dutchman Botic van de Zandschulp 7-6 (7-4) 6-7 (4-7) 6-3 in three hours and 15 minutes.

The Canadian had 36-27 winners but was let down by 43-26 unforced errors, along with converting only two of his 10 break points.

Van de Zandschulp had failed to take three match points in the second set but showed composure to finish the job in the third.

Wild card Andy Murray was also eliminated in the second round, blowing three set points in the first set before going down to 31st seed Alexander Bublik 7-6 (11-9) 6-3 in two hours and one minute.

Last year's Wimbledon runner-up and Italian sixth seed Matteo Berrettini needed more than two hours to get past world number 86 Holger Rune 6-3 4-6 6-4.

Seventh seed Andrey Rublev defeated Dominik Koepfer 7-5 6-4 to extend his win streak to 10 matches, while 11th seed Hubert Hurkacz beat Oscar Otte 6-3 3-6 6-3.

Other seeds to be eliminated were 22nd seed Aslan Karatsev who went down 7-6 (7-5) 6-4 to American Steve Johnson, while 24th seed Marin Cilic lost 6-7 (7-9) 6-3 7-6 (8-6) to Miomir Kecmanovic.

Spanish teenager Carlos Alcaraz secured a spot in the Rio Open final after knocking off top seed Matteo Berrettini followed by countryman Fabio Fognini on Saturday.

Several quarter-finals were squeezed into Saturday's schedule alongside evening semi-finals following Friday's ranout, forcing Alcaraz to play twice along with Diego Schwartzman who also progressed to Sunday's decider.

Alcaraz first defeated top seed and 2021 Wimbledon finalist Berrettini in three sets, triumphing 6-2 2-6 6-2 in two hours and two minutes.

The 18-year-old Spanish seventh seed, who reached last year's US Open quarter-finals, backed that up with a straight-sets win over Fognini, 6-2 7-5.

"It means a lot to me," Alcaraz said post-match. "I surprised myself to be able to win two matches in a row in the same day. It's tough to win one match, two is even tougher."

Third seed Schwartzman got past fellow Argentine Francisco Cerundolo 7-6 (7-4) 6-3 in a two-hour-and-two-minute semi-final, having won through earlier in the day 7-6 (7-3) 4-6 6-4 against Pablo Andujar.

The top two seeds will meet in the Delray Beach Open final in Florida after wins by Cameron Norrie and Reilly Opelka on Saturday.

First seed Norrie got past American fourth seed Tommy Paul 6-3 6-3 in one hour and 16 minutes. Norrie had endured a slow start to the calendar year, but will now play for a third ATP Tour title.

Second seed Opelka had a tougher outing, needing three hours to overcome John Millman 7-6 (10-8) 6-7 (3-7) 7-6 (7-4). In a match which only saw two breaks of serve,

Opelka, who won last week's Dallas Open title, sent down 16 aces and won 82 per cent of his first serve.

Top seed Cameron Norrie is through to the semi-finals of the Delray Beach Open after beating Sebastian Korda in three sets.

Norrie eventually overcame the American fifth-seed after a final set tie-break, winning 6-2 1-6 7-6 (7-4).

The Brit's tenacity was key, saving seven of 10 break points, and he will now face another American, Tommy Paul, in the final four in Florida after he beat qualifier Stefan Kozlov 6-3 6-1.

The other semi-final will be contested between Reilly Opelka and John Millman after they bested Adrian Mannarino and Grigor Dimitrov respectively.

Opelka was taken to a third set by his French opponent before winning 7-6 (7-2) 3-6 6-1, hitting 19 aces on his way to victory.

Millan proved too good for third seed Dimitrov winning 6-4 6-4 in an hour and 34 minutes where the Australian's return was a highlight.

At the Rio Open, rain washed out many of the scheduled matches on Friday, with Diego Schwartzman against Pablo Andujar and Miomir Kecmanovic against Francisco Cerundolo both cancelled.

Matteo Berrettini and Thiago Monteiro were finally able to finish their round of 16 match at 11.35pm local time, with the Italian securing victory 6-4 6-7 (6-8) 6-3.

He will play seventh seed Carlos Alcaraz who overcame Federico Delbonis 6-4 7-6 (7-1) after their match was pushed back, starting not long prior to midnight local time.

Just months ago, there were doubts over Rafael Nadal's future. Now, he is a win away from a record-breaking major triumph.

Nadal overcame Matteo Berrettini 6-3 6-2 3-6 6-3 in the Australian Open semi-finals on Friday, reaching his 29th grand slam decider.

The Spaniard is a win away from a 21st grand slam title, which would break his tie with Roger Federer and Novak Djokovic for the most won by a man.

Such events looked incredibly unlikely just months ago.

Nadal ended his 2021 season in August after playing just seven events, a persistent foot injury not only derailing his season but threatening his career.

"Everybody around me, me included, of course, but everybody around me had a lot of doubts. Not about the Australian Open, no, but about coming back on the Tour because the foot was bothering me a lot of days," Nadal said after his third-round win over Karen Khachanov.

"Of course, still today there are doubts because the foot, as I said the other day, is an injury we cannot fix … so we need to find a way that the pain is under control to play, to keep playing. That's the goal.

"Honestly, I was not able to practice very often. But when I was practising, the feeling on the ball was quite good. There have been a lot of months without competing. The movements, all this stuff, you need to recover day by day. There is no way to recover those things without competing. That's what I need, keep playing. Already three and three, so six matches on my back, and positive ones. Every day a little bit better, so I'm happy for that."

After a four-month absence, Nadal made his return at an exhibition in Abu Dhabi in December. Days later, he tested positive for COVID-19.

Still, he made the trip to Australia, winning his 89th ATP Tour title at the Melbourne Summer Set, his first hard-court crown since February 2020.

That success was incredible, given Nadal played just 14 tournaments in total in 2020 and 2021.

"Of course, when you are getting a little bit older, all the comebacks are tougher," Nadal said after beating Marcos Giron in the opening round. "This has been especially, well, difficult because it's not only a comeback from an injury, it's a comeback trying to be back on the Tour after almost two years playing not many events with the virus.

"If you remember in 2020 I only played here and Acapulco, then I just played in Rome, Roland Garros, Paris and London. Six events.

"In 2021 I played just here and then [it] was clay, Monte Carlo, Barcelona, Madrid, Rome, Roland Garros. Washington, yeah. Another six events – 12 events in two years are not many. If we add that I was not able to practice very often, too, it's a really tough one, no?

"But here I am. I am super happy about all the work that we have done to try to be back. We are here enjoying the tennis, and that's it. We're going to keep trying hard."

Nadal is back. Not just back playing, but back fighting his way into grand slam finals, and back in position to make more history.