Andy Murray suffered a third successive first-round defeat, as he was beaten in straight sets by Marcos Giron at the BOSS Open.

The three-time major champion fell at the first hurdle for the seventh time this season, with Giron prevailing 6-3 6-4 after 75 minutes in Stuttgart.

Giron, who was runner-up to compatriot Tommy Paul in Dallas in February, broke in game six as he won nine out of 10 points, before going on to take the opening set.

Murray - a Stuttgart finalist in 2022 - looked to respond as he won eight of the opening nine points at the start of the second.

However, he saw two break points go begging as Giron held before breaking to 15 in game three.

It proved decisive for the American, who clinched victory with a love hold to set up a last-16 clash with Jack Draper.

Data Debrief: Murray set to drop out of world's top 100

Giron hit seven aces and won 80 per cent (33 out of 41) of his first-serve points on the way to claiming his first ATP win over a current or former world number one.

The 999th singles match of Murray's career ended in an 11th defeat of 2024. Having not won a completed match since beating Tomas Etcheverry at the Miami Open, the 37-year-old will drop out of the world's top 100 next week for the first time since January 2022.

Jack Draper vomited into a courtside bin after overcoming struggles with the Melbourne heat to defeat Marcos Giron at the Australian Open in his first ever five-set match.

It is a measure of how inexperienced the 22-year-old still is at the highest level that he had never previously played a match that went the distance, and he looked in serious trouble at two sets to one down against American Giron.

But Draper has been working hard on his physical conditioning and it paid off as he fought back to win 6-4 3-6 4-6 6-0 6-2 after three hours and 20 minutes.

As soon as he had shaken hands with Giron after a final gruelling rally he ran to the bin to be sick, and it was several minutes before he was able to walk off the court.

He will now have to try to recover for a second-round match, against 14th seed Tommy Paul, on Thursday, when temperatures are at least forecast to be much lower.

It was early afternoon when Draper and Giron took to a baking Court Eight under a cloudless sky.

The British number four only arrived in Melbourne on Saturday night after reaching his second ATP Tour final in Adelaide, meaning he was full of confidence but also potentially jaded.

The match was dominated by punishing rallies from the start, with Draper getting the better of five straight breaks of serve and narrowly hanging on to his advantage.

But the momentum began to swing Giron’s way in the second set as the physicality of the match took its toll on Draper.

After Giron levelled the match, the 22-year-old called the trainer to have his pulse taken and blood pressure checked.

He carried on but was unable to chase down the sort of shots he had got to in the first set and his race looked run when Giron opened up a two sets to one lead.

He took another off-court break to change his clothes and came out for the fourth set with a game plan to up the aggression and shorten the points.

It worked superbly, a mixture of thumping groundstokes and feathered drop shots taking California’s Giron, who had appeared untroubled by the heat, out of his comfort zone.

Draper raced through the set, putting him into uncharted territory, but, with shade finally creeping across the court, both his game and his body just about held up to carry him through to his first victory at Melbourne Park.

America's J.J. Wolf was the top seed in action on Tuesday at the Houston Open and he had no issue in his 6-3 6-2 first-round victory over Jordan Thompson.

Wolf, the fifth seed at the United States' only clay court event on the ATP Tour calendar, needed just 75 minutes to send the Australian home early on the back of a rock-solid serving performance.

Thompson was not able to produce a single break point opportunity in the match, and Wolf left an exclamation point on the contest by winning the final five games to run away with the win.

Meanwhile, seventh seed Marcos Giron gave the American crowd another win to cheer for in his 6-0 6-2 demolition of Ecuador's Emilio Gomez.

The chance for the double-bagel was there for Giron after winning the first 11 games to race out to a 6-0 5-0 lead, but he blew four match points as Gomez showed no quit and secured a break to at least take the match over the 60-minute mark.

Eighth seed Tomas Martin Etcheverry prevailed 6-3 6-4 in his all-Argentine clash against Juan Manuel Cerundolo, taking a 3-2 lead in their overall head-to-head meetings after rising 21-year-old Cerundolo took the past two.

German qualifier Yannick Hanfmann booked a second-round matchup against second seed Tommy Paul after a hard-fought 6-4 3-6 6-2 triumph over Japan's Yosuke Watanuki, while Chile's Cristian Garin had little resistance in his 6-3 6-0 victory in a South American showdown against Bolivia's Hugo Dellien.

In the late window, Jack Sock failed to complete the United States clean sweep for the day as he fell 6-2 6-4 to the Czech Republic's Tomas Machac.

World number two Carlos Alcaraz was too good in his Argentina Open quarter-final on Friday, defeating Dusan Lajovic 6-4 6-2.

The 19-year-old is playing in his first tournament of the year, and after dropping a set in his opener against Serbia's Laslo Djere, he had fewer problems against Djere's compatriot.

Alcaraz will play Bernabe Zapata Miralles in an all-Spanish semi-final after he eliminated Buenos Aires' own Francisco Cerundolo 6-3 6-7 (4-7) 6-3.

England's Cameron Norrie had to come from a set behind for the second match in a row to knock out Argentina's Tomas Martin Etcheverry 5-7 6-0 6-3, and he will meet Peru's Juan Pablo Varillas in the other semi-final.

Varillas collected arguably the biggest win of his career against world number 20 Lorenzo Musetti, and he is now two wins away from his first ATP Tour title.

Meanwhile, top seed and world number seven Taylor Fritz is through to the semi-final of the Delray Beach Open after fending off the challenge of veteran Adrian Mannarino 7-6 (10-8) 6-4.

Fritz has lost his past two meetings with Mackenzie McDonald, and he will get a chance at redemption after McDonald joined him in the semi-final with a 3-6 6-3 6-4 triumph over Michael Mmoh.

Fourth seed Miomir Kecmanovic joins Fritz as the only seeded players to reach the semi-finals after he saw off Marcos Giron 7-6 (7-5) 6-3, while second seed Tommy Paul was upset as a heavy favourite against Romania's Radu Albot 6-2 6-2.

Playing in his hometown of Buenos Aires, Francisco Cerundolo avenged his younger brother's defeat at the Argentina Open by defeating Yannick Hanfmann 6-2 4-6 7-5 on Tuesday.

Francisco's younger brother Juan Martin had been eliminated by Hanfmann in the qualifying stage, but the fifth seed got one back on the German after leading the break point opportunities 17 to six.

Fifth-seed Cerundolo was the highest seed in action Tuesday, while sixth seed Sebastian Baez fell 3-6 7-6 (7-5) 6-3 to Serbia's Dusan Lajovic.

In the only all-Argentine clash it was Facundo Diaz Acosta prevailing 7-6 (7-5) 7-5 against Federico Coria – who sits over 100 places higher in the rankings – while Roberto Carballes Baena collected a seeded scalp with a 7-5 6-4 win over Spanish compatriot Albert Ramos-Vinolas.

Meanwhile, Australian Open quarter-finalist Ben Shelton was eliminated from his own hometown tournament as the Florida resident was bounced out of the Delray Beach Open 6-4 6-4 by Marcos Giron.

Shelton beat J.J. Wolf to reach that grand slam quarter-final, but Wolf will be moving on after he emerged with a 7-5 6-3 win against Ilya Ivashka. 

Wolf will play France's Adrian Mannarino following his 4-6 6-3 6-4 triumph over Germany's Daniel Altmaier, and Mackenzie McDonald will get a shot at redemption against fifth seed Yoshihito Nishioka after a comfortable 6-2 6-2 success against Taro Daniel.

McDonald and Nishioka have played twice this year – once at the Adelaide Invitational and once at the Australian Open – and Nishioka has won all five sets.

It was also a day 33-year-old Matija Pecotic will never forget, with the world number 784 winning his first ever ATP Tour match by defeating Jack Sock 4-6 6-2 6-2.

World number eight Taylor Fritz is two wins away from his first title of the season after surviving a tough test against Marcos Giron 7-6 (9-7) 3-6 6-3 in Friday's quarter-final at the Dallas Open.

Fritz, who at 25-years-old is seeking the fifth ATP singles title of his career, allowed seventh-seed Giron only one break point opportunity for the entire match. Fritz himself only created two such opportunities, and further illustrating the closely-fought nature of the battle, Fritz edged the total point count 86-85.

With the win, Fritz booked his place against China's Yibing Wu in the semi-final after the 23-year-old defeated 34-year-old French veteran Adrian Mannarino 6-3 6-4.

The other semi-final will be an all-American showdown after J.J. Wolf upset second seed Frances Tiafoe 4-6 6-3 6-4, and 37-year-old John Isner proved too much for Ecuador's Emilio Gomez in a 7-6 (10-8) 7-5 victory.

Meanwhile, Spain's Albert Ramos-Vinolas is one match away from a final in his home country after defeating Joao Sousa 6-4 2-6 6-1 in the quarter-final of the Cordoba Open.

Ramos-Vinolas will play Argentina's Federico Coria for a spot in the decider after he emerged victorious 6-3 3-0 (ret) against compatriot Francisco Cerundolo.

Heading into the quarter-finals, Francisco and his brother Juan Manuel Cerundolo were on a collision course to meet in the final, but now both are eliminated after 21-year-old Juan Manuel fell 6-7 (5-7) 6-4 6-0 to Bolivia's Hugo Dellien.

Dellien will play fourth seed Sebastian Baez in the other semi-final after eliminating Chile's Tomas Barrios Vera 6-1 3-6 6-1.

Top seed and world number eight Taylor Fritz made a winning start to his Dallas Open campaign on Thursday, eliminating Jack Sock 7-6 (7-5) 6-4.

In an all-American showdown, Fritz played a near-flawless match, converting 91 per cent of his accurate first serves into points while not allowing Sock a single break point opportunity.

Fritz will face seventh seed Marcos Giron in the quarter-final after the American defeated Germany's Oscar Otte 6-4 6-3, while the USA's John Isner also advanced past Germany's Daniel Altmaier 6-3 7-6 (7-1).

Earlier in the day, Serbian fourth seed Miomir Kecmanovic was upset by Ecuador's Emilio Gomez 2-6 7-6 (7-4) 6-4 to earn a crack at Isner in the quarter-finals.

Meanwhile, the top seed fell at the Cordoba Open as red-hot 21-year-old Juan Manuel Cerundolo shocked his Argentinian compatriot Diego Schwartzman 7-6 (8-6) 6-1.

It continues a remarkable run for Cerundolo – the defending champion in Cordoba – who has begun 2023 with 14 wins from his first 15 matches, while his older brother Francisco Cerundolo also advanced with a 6-3 3-6 7-5 win over Federico Delbonis.

If the two brothers both win their next two matches, they will meet in the final.

Marcos Giron survived a scare against qualifier Alex Rybakov in the opening round of the Dallas Open on Tuesday, escaping with a 6-4 6-7 (1-7) 6-1 victory.

One of the top seeds in action, Giron is ranked over 300 spots higher than Rybakov, but the underdog put up a serious fight and held up well in all key indicators.

Rybakov had 29 winners with only 17 unforced errors, and he had just two double faults to go with seven aces, but Giron was better in both categories. His talent shone through with 34 winners and 16 unforced errors, while he also had 10 aces and no double faults.

Also in Dallas, French eighth seed Adrian Mannarino secured a 7-6 (8-6) 6-2 win against Steve Johnson, and he will now face Australia's Jordan Thompson following his 6-1 7-5 triumph over Denis Kudla.

Meanwhile, at the Cordoba Open, Argentina's Federico Coria was the top seed to advance after defeating Brazil's Thiago Monteiro 6-7 (5-7) 6-1 6-2.

There was less success for hometown seventh seed Pedro Martinez, who was eliminated 7-6 (7-3) 2-6 6-0 by Chile's Cristian Garin, while Federico Delbonis beat Alejandro Tabilo 6-7 (8-10) 6-2 7-6 (8-6) to earn a shot at second seed Francisco Cerundolo.

World number one Carlos Alcaraz is through to the semi-finals of the Swiss Indoors Basel after easing past Pablo Carreno-Busta in straight sets.

Alcaraz took just under an hour and 40 minutes to overcome his fellow Spaniard and friend 6-3 6-4, getting 67 per cent of his first serves in and winning 77 per cent of those.

Carreno-Busta struggled to keep the US Open champion at bay, facing 12 break points in all, and although he saved nine of them, his defiance was ultimately in vain.

"It is difficult to play against a friend like Pablo," Alcaraz said on-court after his win on Friday. "Every day we go and have dinner, lunch, together. Every week and we train together, so it is difficult to play against him.

"I also support him and want him to win every match. On court, there are no friends. You have to be focused and go for the match and that is what I did."

Alcaraz will face third seed Felix Auger-Aliassime in the final four after the Canadian defeated Alexander Bublik 6-2 6-3.

The other semi-final will see Roberto Bautista Agut play Holger Rune after the Spaniard beat Stan Wawrinka 7-5 7-6 (7-5) and the Danish teenager defeated Arthur Rinderknech 7-6 (7-0) 6-2.

In Austria, top seed at the Vienna Open Daniil Medvedev beat Jannik Sinner 6-4 6-2 to advance to the last four, where he will play Grigor Dimitrov after the Bulgarian overcame Marcos Giron 6-3 4-6 6-4.

The winner of that contest will face either Denis Shapovalov, who beat Dan Evans 6-3 6-3, or Borna Coric after the Croatian came through against Hubert Hurkacz 6-4 6-7 (2-7) 7-6 (7-5).

In an all-American final at the San Diego Open, Brandon Nakashima defeated Marcos Giron 6-4 6-4 to capture the first ATP Tour title of his career.

Nakashima, 21, was playing in the third final since arriving on the ATP Tour, having lost the deciders at both the Atlanta Open and the Los Cabos Open as a teenager back in 2021.

Against Giron, the first set lasted just 35 minutes as San Diego native Nakashima converted the only break point opportunity of the frame, while winning 80 per cent (20-of-25) of his service points.

In a spectacularly efficient display, Nakashima hit 15 winners and only one unforced error, while adding six aces with no double faults.

He cooled off slightly in the second set, but it was still more than good enough, posting another 15 winners with five unforced errors and grabbing a break of serve in the opening game.

Giron would finally nab his first break of the contest in a game where he converted on his fourth opportunity, but Nakashima immediately answered to jump ahead 4-2 and serve it out cleanly.

With the win, Nakashima will rise into the top 50 of the world rankings for the first time when it is next updated.

Local hope Brandon Nakashima will take on Marcos Giron in the San Diego Open final after the latter shocked top seed Daniel Evans in Saturday's semi-finals.

World number 58 Giron upset Evans 6-3 7-5 in one hour and 46 minutes, qualifying for his maiden ATP Tour final.

San Diego native Nakashima progressed into the decider after getting past Australian Christopher O'Connell 6-4 7-6 (7-3).

Nakashima's triumph means he is into his first tour-level final of the season and it has come in familiar territory.

The fifth seed needed one hour and 50 minutes to beat O'Connell, who had the edge in the key statistics, including 8-7 aces, 34-31 winners and 13-16 unforced errors.

But Nakashima came up big when it mattered, managing the only break of the match in the first set, before triumphing in a tiebreak.

Giron produced the surprise result against world number 25 Evans, who was chasing his first-ever ATP Tour title.

The American sent down 11 aces, while he also hit 40-25 winners. Evans was unable to convert any of the three break points he generated throughout the match.

Top seed Daniel Evans is through to the last four at the San Diego Open after defeating Constant Lestienne 6-1 6-3 in Friday's quarter-final

It was perhaps a closer contest than the final score indicates, with Evans creating 13 break point opportunities while Lestienne created 11, but the Englishman was able to save 10 of the 11 he faced while converting five himself.

Ultimately the difference between the two players was Evans' ability to avoid wasteful errors, posting 23 winners with 12 unforced errors while Lestienne had 15 winners with 21 unforced errors.

Evans will play third seed Marcos Giron for a spot in the final after the American beat Australia's James Duckworth 7-6 (7-5) 6-3.

It was a match that was decided by the efficiency of Giron, who was more accurate with his serve, landing 59 per cent of his first serves fair compared to 47 per cent for Duckworth.

The Australian actually created more break point chances – eight to three – but while he converted two of his eight chances, Giron turned all three into breaks.

While the top half of the draw played out as the seeding predicted, there was an upset in the late window as Christopher O'Connell eliminated second seed Jenson Brooksby 6-4 4-6 7-5.

The Australian had a clear serving advantage, smacking 14 aces compared to four for Brooksby, and he also racked up a massive 50 winners with 16 unforced errors. Brooksby had 24 winners with 21 unforced errors.

Despite being the better shot-maker on the day, O'Connell had to save two match points to keep his chances alive, and then broke Brooksby as the American tried to serve it out, rattling off four consecutive games to end the match.

O'Connell will face Brandon Nakashima in the semi-final after he emerged victorious 6-3 4-6 6-4 against Daniel Elahi Galan.

Nakashima has now won five of his past six matches, with the only loss in that stretch coming against Jannik Sinner in the US Open.

Marcos Giron was the highest seed in action on Wednesday at the San Diego Open, and he had little trouble dispatching Tomas Martin Etcheverry 6-4 6-3.

Giron, the third seed, was a force a from the baseline, collecting 18 winners in the first set, while Etcheverry could only muster six. While he was not as dominant in the second frame, Etcheverry helped him out with 14 unforced errors and five winners.

Giron will meet James Duckworth next after the Australian defeated America's Mitchell Krueger 6-3 7-6 (7-4).

Duckworth has now won six of his past eight matches, and he showed off his impressive serve against Krueger, winning the ace count 11-to-one.

Meanwhile, Mackenzie McDonald has earned a shot against his American compatriot and second seed Jenson Brooksby after hammering Switzerland's Henri Laaksonen 6-0 6-2.

McDonald was strong in all areas, but particularly in limiting his errors, finishing the match with no double faults and six unforced errors with 19 winners.

Rising Chilean talent Alejandro Tabilo used his powerful serve to overwhelm the similarly hard-serving Steve Johnson, winning 7-5 6-2.

Tabilo served 11 aces with no double faults, and won 80 per cent (41-of-51) of his total points on serve, while Johnson had three double faults with his seven aces and could only manage a 60 per cent (34-of-57) success rate on serve.

In an all-Australian matchup, Christopher O'Connell advanced past Jason Kubler after the latter was forced to retire due to injury with the match tied at 4-6 6-3 heading into the last set.

Rafael Nadal made a strong start to his Australian Open campaign, brushing past Marcos Giron in the opening round on Monday.

The Spanish superstar outclassed American Giron in a resounding 6-1 6-4 6-2 victory on Rod Laver Arena.

Nadal, who can claim the outright lead for most grand slams won by a man if he clinches his 21st in Melbourne, was in good form.

Playing his first major since last year's French Open, Nadal – the only former champion in the draw following Novak Djokovic's deportation from the country – was never troubled by Giron.

Nadal reeled off five consecutive games to take the opening set in 24 minutes.

His excellent first set was highlighted by two brilliant winners to break for 5-1 as he completely dominated Giron.

Nadal capitalised on his momentum by breaking in the opening game of the second set, Giron finally stopping the run by holding for 1-2.

The Spaniard maintained his lead and was forced to serve out the set, doing so to 15 to take complete control.

A backhand pass saw Nadal break again in the opening game of the third set on his way to a comprehensive win, with Thanasi Kokkinakis or Yannick Hanfmann awaiting him in the second round.

DATA SLAM: Nadal makes no mistake in opener

Only twice in his illustrious career has Nadal lost in the opening round of a grand slam – at Wimbledon in 2013 and the 2016 Australian Open.

But since his defeat to Fernando Verdasco in Melbourne six years ago, Nadal has not lost a set in the Australian Open first round, continuing that record against Giron.

WINNERS/UNFORCED ERRORS
Nadal – 34/26
Giron – 10/23

ACES/DOUBLE FAULTS
Nadal – 7/2
Giron – 2/2

BREAK POINTS WON
Nadal – 5/9
Giron – 0/2

Top seed Aslan Karatsev exited the Astana Open at the last-16 stage with a straight-sets defeat to Emil Ruusuvuori on Thursday.

World number 84 Ruusuvuori saved a set point in the first-set tie-break on his way to a 7-6 (8-6) 6-4 victory and will now face Ilya Ivashka for a place in the semi-finals.

There was nearly another upset as home hopeful Alexander Bublik, seeded second, had to recover from a set down to overcome Miomir Kecmanovic 2-6 6-3 7-5.

Carlos Taberner awaits Bublik in the next round after the Spaniard beat Egor Gerasimov 5-7 7-6(5) 7-5.

Kwon Soon-woo and James Duckworth saw off Dusan Lajovic and Filip Krajinovic respectively in straight sets to remain a course for glory.

At the Moselle Open in Metz, meanwhile, Gael Monfils took out Philipp Kohlschreiber 7-6(2) 6-4 to reach the quarter-finals on home soil.

Tournament favourite Hubert Hurkacz made light work of 2016 champion Lucas Pouille with a 6-2 6-3 victory to set up a meeting with Andy Murray in the quarter-finals.

Elsewhere on Thursday, German qualifier Peter Gojowczyk proved too strong for Karen Khachanov and will now face Marcos Giron, who upset fourth seed Alex de Minaur.