Novak Djokovic is safely into the third round, but there were a couple of big shocks on day three of the US Open.

Seventh seed Stefanos Tsitsipas was knocked out in five sets by Dominic Stricker, a qualifier ranked 128 in the world.

Then, in the night session, fifth seed and last year’s runner-up Casper Ruud fell foul of China’s world number 67 Zhang Zhizhen.

British qualifier Lily Miyakazi’s run came to and end in the second round.

Here, the PA news agency looks back at day three at Flushing Meadows.

Pic of the dayShock of the day

Chocolate-loving Dominic Stricker caused a major upset at the US Open by knocking out seventh seed Stefanos Tsitsipas.

The chubby-cheeked 21-year-old qualifier from Switzerland, ranked 128 in the world, stunned two-time grand slam finalist Tsitsipas with a 7-5 6-7 (2) 6-7 (5) 7-6 (8) 6-3 victory to reach the third round.

The former French Open junior champion recently admitted his coach had told him to cut down on chocolate and cookies.

Yet it was Athens-born Tsitsipas who was left feeling sour after a four-hour slog on the Grandstand Court.

Brit watch

Miyazaki’s US Open adventure was ended in the second round by Olympic champion Belinda Bencic.

The 27-year-old came through three matches to qualify at Flushing Meadows for the first time and then picked up a maiden grand slam win against Margarita Betova in round one.

But the world number 198 found 15th seed Bencic, of Switzerland, too tough a nut to crack as she bowed out 6-3 6-3.

Miyazaki still leaves New York with the consolation prize of having virtually doubled her earnings for the year with a £98,000 pay day for winning her first-round match.

There were victories in the doubles for Jamie Murray, with Michael Venus, Joe Salisbury alongside partner Rajeev Ram, Lloyd Glasspool with Harri Heliovaara. and British pair Julian Cash and Henry Patten.

Quote of the dayFallen seeds:

Women: Petra Kvitova (11), Victoria Azarenka (18), Beatriz Haddad Maia (19), Magda Linette (24)
Men: Casper Ruud (5), Stefanos Tsitsipas (7), Francisco Cerundolo (20), Chris Eubanks (28).

Who’s up next?

Andy Murray kicks things off on Arthur Ashe against Bulgarian ninth seed Grigor Dimitrov. Fellow Brits Dan Evans, Cameron Norrie, Jack Draper and Katie Boulter are also in action along with Jodie Burrage, who faces the match of her life against second seed Aryna Sabalenka on Louis Armstrong.

Novak Djokovic stands alone at the pinnacle of men’s tennis after defeating Casper Ruud to win his 23rd grand slam title at the French Open.

Since claiming his first at the Australian Open in 2008, Djokovic has been pursuing Roger Federer and Rafael Nadal through the history books but now he has surpassed both having broken the record he jointly held with Nadal.

Djokovic’s 7-6 (1) 6-3 7-5 victory over Ruud draws him level with Serena Williams and he could equal Margaret Court’s all-time singles mark at Wimbledon next month.

The Serbian, meanwhile, also becomes the first man ever to win at least three slam titles at all the major tournaments – a measure of his all-round greatness.

Ruud had impressed in making it back to the final, where he won only six games against Nadal last year, and was looking for his first title in his third final having also lost to Carlos Alcaraz at the US Open.

He had failed to win a set in four previous matches against Djokovic, though, and missed his chance here in an 81-minute opener before the Serbian pulled away for his 21st consecutive slam victory.

This was the most humid day of the fortnight and, with black clouds looming, it appeared the match would be played under the roof on Philippe Chatrier only for the cover to be removed just before the start.

Ruud’s best chance was to make a fast start and take advantage of the nerves Djokovic would surely be feeling so close to a goal he has been pursuing relentlessly for years.

On his only previous shot at striking out on his own, at the US Open in 2021, he had rather frozen in sight of the line, losing to Daniil Medvedev in the final.

Ruud had read the script and came out sharp, exploiting Djokovic’s unusually leaden footwork with high shots to push his opponent back and breaking in the second game when the Serbian shanked a smash – the one remaining weakness in his game.

Djokovic had NFL great Tom Brady in his player box, while Kylian Mbappe and Zlatan Ibrahimovic were also in the crowd, and they witnessed Djokovic claw his way back, breaking in the seventh game after a punishing rally that ended with Ruud netting an overhead.

Djokovic refused to miss in another long rally after Ruud created a break point in the next game, but it was the third seed cursing himself for a missed opportunity at 4-4, with his irritation compounded when he lost his balance and fell sprawling to the clay.

Djokovic also complained vociferously to the umpire about the quick turnaround between games as the set extended beyond the hour mark.

The longer it went on, the more important it became to win it, and Ruud was two points away on Djokovic’s serve after winning a point with a tweener lob but that was as close as he would come.

One of Djokovic’s greatest strengths is the ability to raise his level at key moments and he won an absurd sixth tie-break of the tournament without making a single unforced error.

Given Djokovic had won his previous 100 slam matches once he had taken the opening set, it was a crushing blow for Ruud, and that was compounded when he dropped serve in the second game of the second set.

Djokovic now looked fully settled, with his forehand purring, and, although Ruud saved two set points at 2-5, the door was firmly shut in his face in the next game.

Ruud was now clinging on by his fingernails but he was determined not to allow Djokovic to run away with it, as Nadal had last year.

The Norwegian found a better rhythm on his serve and applied some pressure to Djokovic, although he was left cursing his luck when his opponent benefited from a lucky netcord down 0-30 at 3-4, giving the French crowd a final chance for a round of booing.

The question seemed to be when Djokovic would make his move, though, and it came at 5-5, a series of superlative groundstrokes earning him the break, and moments later his moment of history.

Nadal was among the first to hail the Serbian, tweeting: “Many congrats on this amazing achievement @DjokerNole. 23 is a number that just a few years back was imposible to think about, and you made it! Enjoy it with your family and team!”

Carlos Alcaraz survived a major scare in the opening match of his Madrid Open title defence as he came from behind to beat Emil Ruusuvuori.

The defending champion, who defeated Alexander Zverev in last year's final, was twice broken in the opening set by Ruusuvuori but responded well to prevail 2-6 6-4 6-2.

Alcaraz hit 36 winners to his opponent's 23 to reach the last 32, where Grigor Dimitrov awaits after defeating Gregoire Barrere 7-6 (8-6) 7-6 (7-2). 

"It was really tough. I would say I was about to lose," Alcaraz said in his on-court interview. "It was really tough. Emil played unbelievably, but I am really happy to get through that."

There was a shock result elsewhere as third seed Casper Ruud lost 6-3 6-4 to Matteo Arnaldi, who had never previously claimed victory over a top-10 opponent.

Arnaldi previously eliminated Benoit Paire and will now take on Jaume Munar – the Spaniard advancing after Tallon Griekspoor retired when a set behind in their second-round tie.

Monte Carlo Masters winner Andrey Rublev continued his good form on the clay courts with a 7-5 6-4 win against Stan Wawrinka.

Nuno Borges will face reigning champion Carlos Alcaraz in the second round of the Barcelona Open after a 6-2 6-3 triumph over Ilya Avashka on Monday.

Borges created a remarkable 20 break points, converting only five but still comfortable against his 61st-ranked opponent.

That sets up a clash with number one seed Alcaraz, who beat Pablo Carreno Busta in the 2022 final.

Ben Shelton's 7-5 6-4 success over countryman Mackenzie McDonald means he will take on Casper Ruud, while Bernabe Zapata Miralles will play Roberto Bautista Agut in an all-Spanish second-round affair after earning a routine 6-2 6-2 win over unfancied Attila Balazs.

Meanwhile, Emil Ruusuvuori beat Alexander Bublik in Barcelona for a second straight year to set up a second-round meeting with fifth seed Frances Tiafoe.

At the BMW Open in Munich, 2022 winner Holger Rune will open his defence against Yannick Hanfmann after the German battled from a set down to beat Thiago Monteiro 6-7 (3-7) 7-6 (7-5) 6-2.

Marcos Giron reached the second round with a 6-1 5-7 6-2 victory over Roberto Carballes Baene.

Lorenzo Musetti stunned Novak Djokovic to seal a "dream" victory and a quarter-final spot in the Monte Carlo Masters.

Falling to a 4-6 defeat in the first set, Musetti responded to win 7-5 in the second and 6-4 in the third following a rain delay.

The 21-year-old overcame the world number one in a mammoth two-hour, 54 minute encounter and capitalised on weak serves from the Serbian – breaking his opponent eight times en route to a career high victory.

Emotions were high for Musetti, who said afterwards: "I am struggling not to cry. It is an emotional win because it was a really long match. Three-hour match and suspended by rain.

"It was not easy conditions because it was a little bit windy and cold. Not like we used to play in the recent days. I am really proud of myself and I can see on the screen. I am struggling not to cry because it is a dream for me."

Musetti's reward is a clash with Jannik Sinner in the quarter-finals, who trailed Hubert Hurkacz by a set and a break before rallying to a 3-6 7-6 (8-6) 6-1 triumph – sending him into the last-eight in six of the seven events he has played this season.

Elsewhere, Andrey Rublev earned a 50th tour-level win on clay with a 7-6 (6-4) 6-2 victory over Karen Khachanov, who was his doubles partner earlier this week before the pair suffered elimination against Wesley Koolhof and Neal Skupski.

Rublev will meet German qualifier Jan-Lennard Struff in the next round, who secured a major upset earlier in the day by eliminating world number four Casper Ruud.

A 6-1 7-6 (10-8) victory earned Struff his first top 10 win since June 2021, when he defeated Daniil Medvedev in Halle, and advances to his first ATP Masters 1000 quarter-final since Cincinnati in 2020.

Casper Ruud clinched his 10th career ATP title with a straight-sets victory over Miomir Kecmanovic in Sunday's Estoril Open final, while Roberto Carballes Baena won the Grand Prix Hassan II.

Having enjoyed the best season of his career in 2022, Ruud was bidding for his first trophy success of 2023 in Portugal, and the world number five made a flying start to his clash with Kecmanovic.

Ruud wrapped up the opener in just 36 minutes, taking control with a huge forehand winner to break in just the third game.

The Norwegian navigated two three-set contests in order to reach the showpiece, and it looked like another of his matches may go the distance when Kecmanovic recovered to force a second-set tie-break.

However, a dipping backhand saw Ruud secure the second of two crucial mini breaks, and he took the first of his three championship points to cap a fine week with silverware, sealing a 6-2 7-6 (7-3) win.

Elsewhere, Carballes Baena won just his second career title, triumphing on the clay in Marrakesh where he beat Alexandre Muller 4-6 7-6 (7-3) 6-2.

France's Muller showed no signs of being overawed on his first final outing as he took the opener in impressive fashion, but Carballes Baena edged a tie-break in the second before dominating the decider.

Carballes Baena's triumph – recorded in just under three hours – gave him his first title since the 2018 Ecuador Open, which also came on his favoured clay surface.

Casper Ruud defeated Quentin Halys in a third-set tie-break to reach the final of the Estoril Open, where Miomir Kecmanovic awaits after defeating Marco Cecchinato.

The number one seed, competing in his first semi-final of the season, prevailed 6-4 3-6 7-6 (7-2) in Portugal to move within one match of a 10th singles title.

Ruud broke his opponent's serve in the opening game and saw out the first set, but Halys – competing in his first ATP Tour semi-final – hit back in the second to prolong the match.

Both men held as the contest went the distance, but Ruud's quality told as he raced 3-0 ahead in the deciding tie-break and did not look back as he set up a final with Kecmanovic.

World number 40 Kecmanovic needed a little over an hour to beat sixth seed Cecchinato, who had surprised Alejandro Davidovich Fokina in the previous round.

Kecmanovic, aiming to add to his only previous singles success in Kitzbuhel three years ago, held serve throughout to claim a 6-3 6-1 win over the 2018 French Open semi-finalist.

Elsewhere on Saturday, the final seeded player fell at the Grand Prix Hassan II as Dan Evans was defeated 2-6 6-4 6-2 by Roberto Carballes Baena.

Carballes Baena has now eliminated three seeded players and will face Alexandre Muller in Sunday's final after the Frenchman saw off Pavel Kotov in straight sets.

Muller edged a first-set tie-break and proved too strong in the second as he saw out a 7-6 (7-3) 7-5 victory in Marrakesh.

Casper Ruud is through to the final four of the Estoril Open after a routine 6-3 6-0 victory against defending champion Sebastian Baez on Friday.

The number one seed dominated his Argentine opponent from the moment the first set went to 3-3, winning nine-straight games from there to ease to victory.

Ruud did need to save four break points in the second game of the second set, but his ability to hold serve seemed to end any resistance that Baez could muster.

The Norwegian will face Frenchman Quentin Halys in the semi-finals after his own straight-sets triumph over Dominic Thiem

Halys reached his first ever ATP Tour semi after recording a 6-1 6-4 win over the former world number three in just one hour and 19 minutes.

The other semi-final will see Miomir Kecmanovic take on Marco Cecchinato after the latter stunned third seed Alejandro Davidovich Fokina in straight sets.

The world number 96 claimed a 7-5 7-6 (7-5) victory in the first meeting between the pair to set up a last-four clash with Kecmanovic, who saw off sixth seed Bernabe Zapata Miralles with a comfortable 7-5 6-2 win.

Elsewhere, Dan Evans is the only seed remaining in the Grand Prix Hassan II as he reached the semi-finals by cruising to a 6-3 7-5 triumph over world number 201 Andrea Vavassori in Marrakech.

Evans will face Roberto Carballes Baena next after the Spaniard toppled fourth seed Tallon Griekspoor 6-3 2-6 6-2.

Second seed Lorenzo Musetti was beaten by Alexandre Muller 6-3 1-6 6-4 in a topsy-turvy encounter, and the Frenchman will now face Pavel Kotov in the final four after the Russian defeated Christopher O'Connell in a thriller, 6-3 6-7 (6-8) 7-6 (7-3).

Top seed and reigning champion Carlos Alcaraz dished out a bagel as he continued his outstanding form with a straight-sets victory over Dusan Lajovic to ease into the Miami Open fourth round on Sunday.

Alcaraz, who triumphed at last week's Indian Wells Open, beat the 76th-ranked Serbian 6-0 7-6 (7-5) in one hour and 32 minutes.

The 19-year-old Spaniard hit 26 winners compared to Lajovic's eight, while Alcaraz also sent down three aces on a 75 per cent first serve percentage.

Alcaraz won the first frame to love in 32 minutes, registering his fourth career bagel at ATP Masters 1000 level, equaling the most by a teenager alongside Rafael Nadal.

The world number one will face 2023 Australian Open semi-finalist Tommy Paul in the fourth round after the American got past 20th seed Alejandro Davidovich Fokina 6-3 7-5.

Third seed and 2022 Miami Open finalist Casper Ruud blew a first-set lead to lose 3-6 6-4 6-4 to Botic Van De Zandschulp.

The Dutchman improved his head-to-head record against Ruud to 3-1 with his first-ever top five win, with the Norwegian left to lament converting only two of 15 break points.

Ninth seed Taylor Fritz progressed into the fourth round with a 6-4 6-4 win over Denis Shapovalov, improving his head-to-head record against the Canadian to 4-5. Fritz committed only eight unforced errors and did not face one break point.

Jannik Sinner maintained his excellent hard-court form with his 18th win this season on the surface, as he defeated Grigor Dimitrov 6-3 6-4 in one hour and 28 minutes. The Italian 10th seed will be Andrey Rublev in the next round.

Sixth seed Rublev needed less than an hour to get past Miomir Kecmanovic 6-1 6-2, while compatriot Daniil Medvedev advanced via a walkover against Alex Molcan due to a right hip injury.

Seventh seed Holger Rune cruised past Diego Schwartzman 6-4 6-2, while Finland's Emil Ruusuvuori got past Taro Daniel 6-3 7-6 (7-3).

World number one Carlos Alcaraz wasted no time in advancing to the Miami Open third round with a straight-sets win over Facundo Bagnis in just 64 minutes, while 13th seed Alexander Zverev suffered an early exit on Friday.

Reigning US Open champion Alcaraz eased past Bagnis 6-0 6-2, firing 12 winners and three aces for the match, committing only 11 unforced errors.

The Spaniard won the first set in 24 minutes, marking the first time he has won an opening frame 6-0 at an ATP Masters 100 event. It was also the first bagel he has dished out since beating Bagnis in Umag last year.

"I knew that I needed to be focused for my first match," Alcaraz said after his win, having triumphed in Indian Wells last week. "To start a new tournament is never easy, different conditions.

"I have to be ready to get used to these new conditions, but I was really focused on the match from the beginning, and I'm happy with the way that I played. I try to improve every day."

Alcaraz will face Dusan Lajovic after he beat 30th seed Maxime Cressy 6-4 7-6 (7-2), having knocked off Andy Murray in the first round.

Zverev was the highest seed to bow out on Friday, going down 6-0 6-4 to Japan's Taro Daniel, who beat world number four Casper Ruud last month in Acapulco.

Daniel triumphed in 73 minutes against the German, hitting 17 winners and committing only two unforced errors for the match, while Zverev gave up 18.

The Japanese wild card will meet Emil Ruusuvuori in the third round after the Finn beat 22nd seed Roberto Bautista Agut 6-4 7-6 (7-5) to open up that section of the draw.

Third seed Ruud also had few problems getting past Ilya Ivashka 6-2 6-3 to set up a clash with Botic van de Zandschulp after his three-set win over Alexei Popyrin.

Sixth seed Andrey Rublev overcame J.J. Wolf 7-6 (7-3) 6-4, having been broken in the opening game of what was a tight contest.

Jannik Sinner beat Laslo Djere 6-4 6-2, marking his 16th win out of 20 appearances at the Sunshine Double (Indian Wells and Miami), with only three other players – Novak Djokovic, Alcaraz and Hubert Hurkacz – having as many wins within their first 20 matches.

Ninth seed Taylor Fritz defeated fellow American Emilio Nava 6-4 6-1, and will face Denis Shapovalov in round three after he beat Guido Pella 6-3 3-6 6-3.

American 16th seed Tommy Paul came from a set down to beat Marc-Andrea Huesler 5-7 6-3 6-4, while seventh seed Holger Rune beat Martin Fucsovics 6-3 7-5.

Two-time Miami Open champion Andy Murray has been eliminated in the first round of this year's event after a shock 6-4 7-5 loss to world number 76 Dusan Lajovic on Wednesday.

Murray, ranked 53rd in the world, could not find his usual return with Lajovic winning 72 per cent of second-serve points, prevailing in one hour and 38 minutes.

The Serbian claimed only his fourth win out of 16 matches on hard courts since the start of last year, holding his nerve after failing to serve out the match at 5-4 in the second set, converting his third match point in the 12th game.

Lajovic hit 21-14 winners, with Murray committing more unforced errors (15-13). The Serbian converted all three break points he generated.

Former world number six Gael Monfils was forced to retire due to a right wrist injury in his clash with French compatriot Ugo Humbert at 3-3.

Monfils, 36, was playing at only his third event since returning to the ATP Tour following seven months out due to injury.

Argentina's Facundo Bagnis defeated Brazilian qualifier Felipe Meligeni Alves 6-3 1-6 6-4, with his reward a second-round clash with last week's Indian Wells Open winner and top seed Carlos Alcaraz.

World number 50 J.J. Wolf beat world number 48 Alexander Bublik 7-5 6-3 in 79 minutes, earning a second-round clash with sixth seed Andrey Rublev.

World number 74 Martin Fucsovics sent down nine aces as he beat Argentina's Pedro Cachin 6-4 7-6 (7-2) in 107 minutes. Fucsovics will next face seventh seed Holger Rune.

Ilya Ivashka beat Daniel Altmaier 6-2 6-1 to book a second-round clash with third seed Casper Ruud, while Fabio Fognini bowed out, losing 6-4 5-7 6-4 to Jan-Lennard Struff. USA's Brandon Nakashima powered to a 7-6 (7-3) 6-3 victory over Germany's Oscar Otte.

Two of the Indian Wells Masters' top-three seeds have failed to reach the final 16 after Casper Ruud fell 6-4 7-6 (7-2) at the hands of Cristian Garin on Sunday.

Ruud, the third seed, joined second seed Stefanos Tsitsipas with an early exit after a timid display, with just 17 winners to go with 17 unforced errors against Chile's Garin.

Meanwhile, Garin took his opportunity against the world number four with both hands, rattling off 39 winners with 24 unforced errors as he made the decision to take the match on and not die wondering.

Garin, who already defeated 29th seed Yoshihito Nishioka in the second round, will meet his third seeded opponent in a row in the quarter-final when he takes on Spain's 23rd seed Alejandro Davidovich Fokina.

Davidovich Fokina eliminated 13th seed Karen Khachanov 6-3 1-6 6-4, but it was still a strong day for the Russians as top hopefuls Daniil Medvedev and Andrey Rublev advanced.

Medvedev, the fifth seed, was tested in his 6-2 3-6 6-1 victory over Belarus' Ilya Ivashka, while sixth seed Rublev saw off France's Ugo Humbert 7-5 6-3 without much issue.

Waiting for Rublev in the quarter-final is Briton Cameron Norrie after his 6-7 (5-7) 7-5 6-2 battle against Taro Daniel, while Alexander Zverev beat Emil Ruusuvuori 7-5 1-6 7-5 to book a tantalising clash with Medvedev.

In a poor day for the Australians, Jason Kubler went down 6-3 6-2 against 14th seed Frances Tiafoe, and Jordan Thompson could not follow up his incredible upset against Tsitsipas, falling 6-3 7-6 (8-6) to Chile's Alejandro Tabilo.

World number three Stefanos Tsitsipas has left the Indian Wells Masters without a win after a shock 7-6 (7-0) 4-6 7-6 (7-5) loss to Jordan Thompson on Friday.

Tsitsipas, the second seed with Novak Djokovic not present, received a bye through to the second round, and he showed some rust with three double faults in the opening set. 

Thompson capitalised, with an incredible 21 winners to only two unforced errors in the first set, and he closed it out with 15 winners and four unforced errors in the deciding frame for the biggest win of his career.

The Australian will now meet Chile's Alejandro Tabilo in the third round after he upset 32nd seed Maxime Cressy in a gruelling 7-6 (7-3) 7-6 (15-13) triumph.

Meanwhile, it was smooth sailing for third seed Casper Ruud in his 6-2 6-3 victory over Diego Schwartzman, and a similar story for fifth seed Daniil Medvedev in his 6-4 6-3 result against Brandon Nakashima.

Alexander Zverev, the 12th seed, had no issues in his 6-3 6-1 domination of Pedro Cachin in 77 minutes, and 13th seed Karen Khachanov also took exactly 77 minutes to see off Oscar Otte 6-3 6-3.

England's 10th seed Cameron Norrie breezed past Tung-lin Wu 6-2 6-4, while Italy's 20th seed Matteo Berrettini suffered an early 7-6 (7-5) 0-6 6-3 exit at the hands of Japan's Taro Daniel.

In the late window, after a lengthy weather delay, 14th seed Frances Tiafoe won his all-American showdown against Marcos Giron 6-2 6-2.

Second seed Casper Ruud suffered a shock three-sets second-round defeat to Japan's Taro Daniel at the Mexican Open in Acapulco on Wednesday.

The 2022 US Open and French Open runner-up had struggled past Guido Andreozzi in the first round and followed up that up with a 7-5 2-6 7-6 (7-5) loss to Daniel.

The Japanese qualifier, ranked 125th in the world, won in just under three hours, winning the final three points of the deciding tie-break after Ruud led 5-4.

Ruud had more winners (38-32) but committed 30 unforced errors compared to Daniel's 12.

Taylor Fritz cruised into the last eight with a 6-4 6-4 win over Canada's Denis Shapovalov, setting up a quarter-final with sixth seed Francis Tiafoe, who eased past Feliciano Lopez 6-2 7-6 (8-6).

Fourth seed Holger Rune was too strong for Nuno Borges 6-0 6-2 inside an hour, while eighth seed Alex De Minaur crushed Jacopo Berrettini in just over an hour 6-1 6-0.

Top seed Lorenzo Musetti was a surprise second-round loser at the Chile Open with Jaume Munar triumphing 6-4 6-4 in one hour and 31 minutes.

Fourth seed Diego Schwartzman also bowed out, going down 6-4 4-6 7-6 (7-2) to local Nicolas Jarry.

Jarry will face Yannick Hanfmann in the quarter-finals, while Munar will take on Thiago Monteiro.

Taylor Fritz was forced to come from behind to claim a three-set victory over John Isner in the opening round of the Mexican Open in Acapulco on Monday.

Fritz was among the seeds to progress, alongside Casper Ruud, Holger Rune, Francis Tiafoe and Tommy Paul.

The third seed lost the opening set in 29 minutes but rallied back to win 3-6 6-3 6-4 in one hour and 49 minutes over the big-serving world number 38 Isner.

Fritz claimed his first break of the match in the 17th game before levelling things up at one set each, before breaking Isner at 4-4 in the third and serving out for victory.

The win means Fritz will take on Canada's Denis Shapovalov in the second round after he beat Miomir Kecmanovic in three sets, with the American looking to go one better after being runner-up in Acapulco in 2020.

Second seed Ruud found himself in an almighty battle with Argentina's Guido Andreozzi and eventually prevailed 6-4 4-6 7-6 (7-2).

World number four Ruud, ranked 338 places above his opponent, was broken in the first game of each set but dug deep to get the job done in a little under three hours. 

Fourth seed Rune got past 2023 Australian Open quarter-finalist Ben Shelton 6-7 (7-9) 6-4 6-2.

Sixth seed Tiafoe overcame Japan's Yoshihito Nishioka 7-6 (8-6) 6-4 while 2023 Australian Open semi-finalist Paul beat Emilio Gomez 6-1 7-6 (7-4).

Defending champion Pedro Martinez was bundled out of the Chile Open in the first round after losing 6-2 6-0 to German qualifier Yannick Hanfmann.

Jaume Munar progressed to set up a second-round clash with top seed Lorenzo Musetti after winning 6-0 6-7 (4-7) 7-6 (7-5) against Alejandro Tabilo.

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