Top seed Jessica Pegula bowed out of the Libema Open following a three-set defeat by Aleksandra Krunic in s'Hertogenbosch.

The world number five was ousted 7-6 (7-3) 6-7 (3-7) 6-4 by the 2018 winner of this event, who claimed the fifth top-10 victory of her career and advanced to the quarter-finals.

Now ranked 400th in the world, Krunic recovered from an earlier break in the opening set to force a tie-break, in which she won five straight points to draw first blood.

The Serbian also cancelled out a break before heading into another tie-break, but Pegula reeled off five points on the spin this time to level.

The American was appearing in her first tournament since April, having missed the European clay-court season with a rib injury.

However, she saw two break-point opportunities go begging in the opening game of the deciding set, and Krunic crucially broke in game three before holding out for an impressive victory. 

Later on, Alex de Minaur booked his place in the quarter-finals of the competition after a straight-sets victory over Zizou Bergs. 

The world number nine had to work for his victory over the Belgian, overcoming his opponent 7-5 6-4 to earn his first triumph on a grass court this year. 

Bergs matched his opponent in the opening exchanges, but the Australian would eventually prevail, winning a break-point and following up without dropping a point in the final game. 

De Minaur would again endure a difficult set to confirm the victory as Bergs threatened to level the encounter, but the number one seed again showed his class, finishing the contest in style. 

De Minaur will face either Roberto Bautista Agut or Milos Raonic in the next round.

Data Debrief: Krunic rekindles special memories as de Minaur earns maiden grass win

Krunic will forever have an affinity with s-Hertogenbosch, where she won her only career WTA title six years ago.

And the 31-year-old claimed an impressive scalp here to reach her first WTA quarter-final since 2022 - and first on grass since that 2018 triumph.

De Minaur impressed once again, winning 86 per cent of his first serve points against the Belgian. 

Their meeting in s-Hertogenbosch was the first between the pair, with De Minaur able to overcome his quarter-final defeat to Alexander Zverev at the French Open. 

Alexander Zverev has no interest in recovering fitness as the world number four aims to push to an "absolute limit" at the French Open.

The German overcame Alex de Minaur in straight sets on Court Philippe-Chatrier, progressing to the Roland-Garros semi-finals for a fourth straight year on Wednesday.

Yet that does not tell the whole story as Zverev battled relentlessly to earn his 6-4 7-6 (7-5) 6-4 triumph over the Australian world number 11.

Falling 4-0 and 5-1 down in the second-set tie-break, Zverev seemed to afford De Minaur a route back into the match, only for the fourth seed to come crashing back in a response.

Zverev eventually sealed victory in just under three hours of the quarter-final meeting, and has every intention of pushing himself further for the last-four clash with Casper Ruud.

"Everybody in the press keeps asking me what I do for recovery and the answer is very simple – you don't recover after matches, you recover in the off-season," Zverev said in his on-court interview.

"I have the mindset you have to work harder than everyone else to be the best player. I like to work to my absolute limit. If I do that then playing five sets all of a sudden is not that difficult.

"I've been doing that over many years and I'm happy to be in another semi-final. Hopefully I can win one."

A fourth semi-final appearance in Paris means Zverev will equal Dominic Thiem for the most of any player born since 1990.

Among players with five main draws in the Open Era, Zverev (80.5 per cent) also holds the best winning percentage at Roland-Garros of any player not to have won the singles title at the event.

Ruud will stand in the way of a major final outing for Zverev, who says his battling identity has been embroiled in his mind from a young age.

"I have a coach who's my father who couldn't care less how I feel on the practice court," he added.

"Since I was three years old, it was run here, run there, run for four hours straight. He sometimes forgets I'm two metres tall and can hit a serve 230 kilometres an hour.

"I wish I would be more aggressive sometimes, but if I'm winning, I'm happy."

Alexander Zverev secured his place in the French Open semi-finals for a fourth straight year after overcoming Alex de Minaur on Wednesday.

The world number four will meet Casper Ruud, who progressed with a bye after Novak Djokovic's injury withdrawal, in the last four after a battling 6-4 7-6 (7-5) 6-4 triumph on Court Philippe-Chatrier.

De Minaur overcame Daniil Medvedev in the previous round to earn his first Roland-Garros quarter-final appearance, though it was one to forget as his serving – and Zverev's grit – proved the 11th seed's undoing.

Both players traded a break apiece during an entertaining opening in the French capital, only for De Minaur's double fault to hand Zverev the 4-3 advantage to hold his serve and take the first set.

The Australian snatched a crucial break midway through the second set, yet Zverev – who was warned with a time violation by the umpire for taking too long over his serve – saved a set point to keep his hopes alive.

That was a sign of things to come, too, as Zverev once again fought from 4-0 and 5-1 down in the tie-breaker, somehow clinching a 2-0 lead in the match from a seeming point of no return.

Having failed to level in that cruel tie-break defeat, De Minaur managed to break Zverev late in the third set but the former responded immediately to secure a hard-fought win in just under three hours.

Data Debrief: Zverev continues on song

Zverev extended to 11 straight wins after this victory, with that run including his sixth ATP Masters 1000 title in Rome two weeks prior to the start of this major.

The German is just the 11th man of the Open Era to reach four consecutive semi-finals at the French Open, where a rested Ruud awaits next.

De Minaur, meanwhile, misses out on the chance to become the first Australian man since Pat Rafter in 1997 to make the last four on Parisian clay.

Alex de Minaur is through to the French Open quarter-finals for the first time after coming from behind to upset Daniil Medvedev on Monday.

Despite losing the first set, De Minaur turned on the style to win 4-6, 6-2, 6-1, 6-3 in two hours and 49 minutes on the court.

Medvedev made a confident start but only just won the first set as the Australian hit the net in the final game to give away the victory.

After that, Medvedev required treatment on his foot, and when he came back out, he had few answers to a dominant De Minaur.

The number 11 seed was resolute in defence and raced through the second and third sets before reeling off four games in a row to take the victory and set up a meeting with Alexander Zverev or Holger Rune in the next round. 

Data Debrief: De Minaur makes strides

De Minaur has reached the quarter-finals of a Grand Slam event for just the second time in his career, and the first time since 2020, when he reached the same stage in the US Open.

He has also become the first Australian to reach the men's singles quarter-finals at Roland Garros since Lleyton Hewitt in 2004, 20 years ago.

Darwin Blanch presented little challenge for Rafael Nadal, who dropped just one game in a convincing 6-1 6-0 triumph at the Madrid Open.

Nadal is feeling his way back to fitness, but 16-year-old qualifier Blanch offered little resistance to the 22-time major champion on Thursday.

Making his farewell appearance at the Madrid Open, where he has won five titles, Nadal needed just 64 minutes to progress to round two.

"I think today I played against an opponent with a great future in front [of him], but today, still making mistakes," said Nadal.

"I just tried to be there, be solid all the time without taking a lot of risks. It worked well. I'm happy to be through and I wish him all the very best for the future."

Nadal's reward is a rematch with Alex de Minaur, who he lost to last week in Barcelona.

Data Debrief

This game saw the largest age gap (21 years, 117 days) between two opponents in the history of ATP Masters 1000 events.

Nadal has now registered 57 wins at the Madrid Open, which is 20 clear of any other player. 

Rafael Nadal’s latest comeback bid came to an end as he was well beaten 7-5 6-1 by fourth seed Alex de Minaur at the Barcelona Open.

The 37-year-old was playing just his second tournament in 15 months after suffering another hip problem at his comeback event in Brisbane in January.

And having intimated that this will be his final year before retirement, Nadal’s defeat was likely to mark his final appearance at a tournament he has won 12 times.

Having overcome Italian Flavio Cobolli in the opening round, Nadal faced a much sterner test against the in-form De Minaur and was sent scampering around the court in a tight opening set which was edged by the Australian.

De Minaur went on to step up a gear, securing a double break over the Spaniard and racing over the line behind a strong service game on which he did not drop a single point in the second set.

Jack Draper made the most of a rain delay to defeat wild card Rudolf Molleker and reach the quarter-finals of the BMW Open in Munich.

German Molleker, ranked 179th, had been the better player in the first set but a brief stoppage ahead of the second set changed the momentum of the contest.

Draper began to assert his powerful game after the resumption and lost only two more games, pulling away to claim a 4-6 6-1 6-1 victory.

In the last eight the British number two, who is ranked 46th, will take on either third seed Taylor Fritz or Spanish qualifier Alejandro Moro Canas.

Speaking in an on-court interview, Draper said: “I think Rudy played an amazing level in the first set. The conditions were very rainy and very slow. In the second and third, the sun comes out and I start feeling better. I’m really proud of the way I played.”

Alex de Minaur has defended his Mexican Open title after defeating Norwegian Casper Ruud in straight sets in Acapulco.

The match took just under two hours as the pair battled in long rallies, with the difference being the Australian’s ability to capitalise on break points, nailing three of four while Ruud converted just one of four.

The 25-year-old took an early lead in the first set at 3-1 and served out the rest of the set, while in the second the pair broke each other before de Minaur had the decisive break in the seventh game.

De Minaur won the same competition last year, beating American Tommy Paul, and further solidified his ranking in the top ten.

He has won 10 straight games in Acapulco and is the first player since David Ferrer in 2012 to win back-to-back titles at the tournament.

He defeated Jack Draper in the semi-final after the Englishman retired ill in the third set.

Katie Boulter is enjoying being part of the “circus” surrounding Australian boyfriend Alex De Minaur.

De Minaur is the newest member of the world’s top 10 and the home country’s great hope for a grand slam champion at Melbourne Park in a fortnight’s time.

His relationship with Boulter has generated a lot of attention, with the pair playing mixed doubles together at Wimbledon last summer, and she is happy to share his moment in the spotlight.

“I am a very private person,” she said. “I like to keep myself to myself, my team close, the things that matter most to me away from everything.

“I think it’s definitely been fun to be a part of because it’s been a little bit of a circus, but a good circus. I think it’s awesome that he’s getting the attention that he really does deserve and he’s put the work in for it.

“He’s playing some of the best tennis of his life and it really does fill me with a lot of pride to actually watch him at this moment.

“I feel like I’m sharing him with everyone, which isn’t a bad thing, but it’s definitely a lot. But he’s handled it a lot of his career and he knows how to deal with it and I’m right there next to him.”

View this post on Instagram

A post shared by Katie Boulter (@katiecboulter)

With Nick Kyrgios still sidelined through injury, De Minaur will carry home hopes virtually single-handed, but the 24-year-old sees only positives.

“I’m living my dream,” he said. “I can wake up in the morning and know that I’ve achieved a massive milestone, which was very tough to get to. I didn’t know if I was going to achieve it.

“Now I can look at myself and say that I’ve done it, that I’m a completely different player to what I was last year. It’s exciting because I’ve got bigger and better things to come hopefully.”

Boulter and De Minaur have been together since 2020 but the last 12 months have seen both hit new heights in their career.

Boulter enters the Australian Open ranked 57 and heads into a first-round clash with China’s Yuan Yue full of confidence after a great start to 2024.

At the United Cup in Perth, Boulter claimed the biggest victory of her career over world number five Jessica Pegula and has her sights set on another sizeable leap this year.

“It was huge,” she said of her win over the American. “I’m sure it wasn’t the best match of her career but I felt like I was right there.

“She’s one of the top players in the world and it gives you belief that that can be you and I strongly believe that if I keep working the way that I do that I can do that.”

She continued: “Top 100 has not been my number. I think I did that five years ago and now I really want to keep pushing. Even 50, I’ve ticked that off as well.

“And now it’s time to start getting up to the real business side of tennis and I think the work that we’ve been putting in has given me a great platform this past year to really push on and give these girls a go. Now it just takes a little bit of belief and a lot more hard work.”

British number one Katie Boulter will play mixed doubles with Australian boyfriend Alex De Minaur at Wimbledon.

The pair are one of the highest-profile couples in tennis and, having supported each other court-side on many occasions, they will now be on the same side of the net for the first time.

Boulter and De Minaur, who will face Australian duo Storm Hunter and John Peers in the first round, are not the only off-court couple in the draw.

World number five Stefanos Tsitsipas and Spain’s Paula Badosa, who recently made their relationship public, are also playing together and will take on top seeds Austin Krajicek and Jessica Pegula.

Other notable pairings are all-British duos Heather Watson and Joe Salisbury and Jodie Burrage and Lloyd Glasspool, while Jamie Murray will play with American Taylor Townsend.

Britain’s Neal Skupski and American Desirae Krawczyk, meanwhile, are bidding for their third successive title.

Carlos Alcaraz secured his first grass-court title and top billing at Wimbledon with victory over Alex De Minaur in the final of the cinch Championships.

The 20-year-old Spaniard overtook Novak Djokovic as world number one, and confirmed he will be a major contender to take the Serbian’s crown at SW19 next month, with a commanding 6-4 6-4 win at Queen’s Club.

Alcaraz was playing only his third ever grass-court tournament, and his first outside of two underwhelming visits to Wimbledon.

In his first match he needed a third-set tie-break to get past French journeyman Arthur Rinderknech, but as the week wore on he grew in confidence on the surface and by Sunday looked to the manor born.

Alcaraz will now be top seed at Wimbledon and, on this evidence, has a genuine chance to emulate compatriot Rafael Nadal, who won at Queen’s in 2008 and went on to claim the big one three weeks later.

A break of serve in each set proved enough to overcome Australian number one De Minaur, who competed well but had no answer to the pace and power of the favourite.

For example when De Minaur, 24, created the match’s first break point, at 4-3 in the opener, Alcaraz simply rolled out a 137mph ace.

A high-quality first set swung the way of the top seed when De Minaur sent a backhand wide, and then a forehand long, to gift Alcaraz the break.

The youngster from Murcia wrapped up the 49-minute set with an ace before taking a medical time-out for treatment on his right thigh.

Whatever the issue was, it did not seem to bother Alcaraz too much as he forced another break point at 2-2 in the second – and De Minaur picked the worst possible time to throw in a first double fault.

Victory was confirmed when De Minaur’s return floated long and Alcaraz celebrated an 11th career title, and surely the first of many on the lawns of London.

Alcaraz said: “It means a lot to have my name on the trophy. It was special to play here where so many legends have won. To see my name surrounded by the great champions is amazing.

“I started the tournament not very well, especially my movement on the grass, but it’s been an amazing week.”

De Minaur had been hoping to match his British girlfriend Katie Boulter, who won a first career title in Nottingham last weekend, but he just came up short.

He said: “It’s been a great week for me. We were close but I wasn’t quite able to get it done. Too good from Carlos.”

Daniil Medvedev and Stefanos Tsitsipas progressed to the third round of the Madrid Open but there was no such luck for Felix Auger-Aliassime on Saturday.

Second seed Medvedev cruised past Italian qualifier Andrea Vavassori 6-4 6-3, teeing up a meeting with Alexander Shevchenko, who overcame Jiri Lehecka in straight sets.

Tsitsipas was made to work by Dominic Thiem, but the fourth seed battling from a set down to win 3-6 6-1 7-6 (7-5).

World number 40 Dusan Lajovic provided the shock of the day by defeating seventh seed Auger-Aliassime 6-2 3-6 7-6 (7-5).

Denis Shapovalov, the 21st seed, was another surprise second-round loser, falling 6-7 (4-7) 6-4 7-6 (7-1) to China's Zhang Zhizhen.

Taylor Fritz avoided adding to the list of notable early eliminations in the Spanish capital, the eighth seed battling to a 7-6 (13-11) 6-4 victory over Christopher O'Connell.

Fritz's fellow American Frances Tiafoe progressed with a 6-3 7-6 (7-5) triumph over Argentina's Tomas Martin Etcheverry, while 14th seed Tommy Paul crashed out after a 6-3 7-6 (7-3) defeat to Roman Safiullin.

Seeds Alex de Minaur and Sebastian Baez also navigated their way through to the third round, defeating Marco Cecchinato and Marcos Giron respectively, as did Cameron Norrie at the expense of Yosuke Watanuki.

Hubert Hurkacz prevailed 6-7 (10-12) 7-6 (9-7) 7-6 (8-6) in a thrilling three-and-a-half hour battle against Thanasi Kokkinakis during Saturday's second round of the Miami Open.

It was Hurkacz's first match of the tournament after the eighth seed received a bye through the first round, and he came up against a match-fit Kokkinakis after the Australian went three sets in his opening victory.

The world number nine had to save five Kokkinakis match points before sealing the win with his first chance, three hours and 34 minutes after the contest began.

Kokkinakis was not the only Australian on the day to go down in a gruelling three-setter as 15th seed Alex De Minaur fell 6-7 (5-7) 7-6 (7-3) 7-6 (10-8) to Quentin Halys in three hours and 20 minutes.

It was far smoother sailing for fourth seed Daniil Medvedev in his 6-1 6-2 triumph over Roberto Carballes Baena, giving the Russian his first win since his 19-match unbeaten streak was ended at the hands of Carlos Alcaraz in the Indian Wells Open final.

The biggest upset of the day came from France's Gregoire Barrere as he eliminated 11th seed Cameron Norrie 6-3 6-2, before Adrian Mannarino ensured a great day for the French contingent with a 6-4 3-6 6-1 result against Ben Shelton in the late window.

Fifth seed Felix Auger-Aliassime needed a pair of tiebreakers to dispatch Brazil's Thiago Monteiro 7-6 (7-5) 7-6 (10-8), while big-serving 19th seed Matteo Berrettini came out on the wrong side of some tiebreakers in his 7-6 (10-8) 7-6 (7-5) loss to Mackenzie McDonald.

The skid from 18th seed Lorenzo Musetti continued as the 21-year-old went down 6-4 6-4 to Jiri Lehecka, giving the Italian seven losses from his past eight matches.

Karen Khachanov fought off the challenge of recent Chile Open finalist Tomas Martin Etcheverry 6-1 3-6 6-3, and second seed Stefanos Tsisipas received a walkover as Richard Gasquet withdrew.

Top seed Carlos Alcaraz and reigning champion Taylor Fritz both overcame challenges to progress into the third round of the Indian Wells Open on Saturday.

Alcaraz won 6-3 6-3 over Thanasi Kokkinakis in one hour and 18 minutes in his opening match of the event, which also marked his return from a fortnight out with a hamstring injury.

The Spaniard, who reached the semi-finals at Indian Wells last year, could return to the number one ranking with victory at this year's event in the absence of Novak Djokovic.

Alcaraz hit 21 winners against the 94th-ranked Australian, dropping only one point on serve in the opening frame.

Fritz went a set down against 2023 Australian Open quarter-finalist Ben Shelton but eventually prevailed 4-6 6-4 6-3 in one hour and 53 minutes.

Both players were excellent on serve throughout the contest, with Fritz earning a break in the 10th game of the second set to tie up the match, before swooping again in the sixth game of the decisive frame.

Veteran Andy Murray moved into the third round with a 6-4 6-3 win over Radu Albot, with the Briton to take on countryman Jack Draper next. Draper won 6-4 6-2 over 24th seed Daniel Evans.

Murray had been set to face 15th seed Pablo Carreno Busta in the second round, but he withdrew due to a muscle injury, allowing Albot into the draw as a lucky loser. Murray's win was his first in straight sets since October.

Seventh seed Holger Rune won 7-5 6-3 over American Mackenzie McDonald, progressing to face Stanislas Wawrinka after he toppled 26th seed Miomir Kecmanovic 7-6 (10-8) 6-4.

Ninth seed Hubert Hurkacz got past Australian Alexei Popyrin 6-3 6-3, setting up a third-round clash with 17th seed Tommy Paul who won 6-3 6-3 over Jan-Lennard Struff.

Eighth seed Felix Auger-Aliassime won 7-6 (7-5) 6-4 over Pedro Martinez, while 11th seed Jannik Sinner got past veteran Richard Gasquet 6-3 7-6 (7-2).

Last week's Mexican Open champion and 16th seed Alex de Minaur was the highest seed to be knocked out on Saturday after a 6-4 6-2 loss to Martin Fucsovics.

Alex de Minaur secured his first ATP 500 title on Saturday after coming from behind to defeat Tommy Paul 3-6 6-4 6-1 in the Mexican Open final.

It was a tremendous week in Acapulco for the Australian, having eliminated world number 10 Holger Rune in the semi-final en route to his seventh title overall, with the first six all at the ATP 250 level.

Against Paul, De Minaur blew a pair of break points in the opening set, and then gave up the break in the very next game, allowing the American to serve things out safely to take the first frame.

But mistakes started to creep into Paul's game the longer the match went. After landing 75 per cent of his first serves fair in the opener and avoiding any double-faults, Paul's first serve percentage dropped to 46 in the second, and he committed a pair of doubles.

He committed another two double-faults in the decider to hand De Minaur the early break, and his play from the baseline also deteriorated, hitting just six winners to go with 14 unforced errors.

Known for his resilience, De Minaur had to save five break points to hold serve in the opening game of the third set, but he held his nerve, and churned out five consecutive games as Paul ran out of gas.

The 500 ranking points will see the Aussie climb to 18th in the world, with his career-best mark of 15th now within reach.

Meanwhile, the fairytale continued for Nicolas Jarry at the Chile Open, with the Santiago-born talent electrifying his home crowd with a 1-6 7-6 (7-4) 6-1 semi-final victory over Jaume Munar.

Jarry will get a chance for the second ATP title of his career, and the first since 2019, when he meets Tomas Martin Etcheverry in the final.

Etcheverry emerged victorious 7-5 6-3 in an all-Argentine showdown against third seed Sebastian Baez, earning his first final appearance at this level.

Alex De Minaur secured his first ATP 500 title on Saturday after coming from behind to defeat Tommy Paul 3-6 6-4 6-1 in the Mexican Open final.

It was a tremendous week in Acapulco for the Australian, having eliminated world number 10 Holger Rune in the semi-final en route to his seventh title overall, with the first six all at the ATP 250 level.

Against Paul, De Minaur blew a pair of break points in the opening set, and then gave up the break in the very next game, allowing the American to serve things out safely to take the first frame.

But mistakes started to creep into Paul's game the longer the match went. After landing 75 per cent of his first serves fair in the opener and avoiding any double-faults, Paul's first serve percentage dropped to 46 in the second, and he committed a pair of doubles.

He committed another two double-faults in the decider to hand De Minaur the early break, and his play from the baseline also deteriorated, hitting just six winners to go with 14 unforced errors.

Known for his resilience, De Minaur had to save five break points to hold serve in the opening game of the third set, but he held his nerve, and churned out five consecutive games as Paul ran out of gas.

The 500 ranking points will see the Aussie climb to 18th in the world, with his career-best mark of 15th now within reach.

Meanwhile, the fairytale continued for Nicolas Jarry at the Chile Open, with the Santiago-born talent electrifying his home crowd with a 1-6 7-6 (7-4) 6-1 semi-final victory over Jaume Munar.

Jarry will get a chance for the second ATP title of his career, and the first since 2019, when he meets Tomas Martin Etcheverry in the final.

Etcheverry emerged victorious 7-5 6-3 in an all-Argentine showdown against third seed Sebastian Baez, earning his first final appearance at this level.