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Miomir Kecmanovic

Alcaraz breezes into Argentina Open semi-final, Paul falls in Delray Beach upset

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.

Alcaraz into Argentina Open final in first tournament after injury, Fritz reaches Delray decider

Alcaraz, who had not played since the Paris Masters in early November due to abdominal and right leg injuries, triumphed 6-2 6-2 in one hour and 17 minutes.

The 19-year-old Spaniard will face second seed Cameron Norrie in Sunday's decider, with the Briton needing almost two hours to overcome Peruvian qualifier Juan Pablo Varillas 7-6 (7-5) 6-4.

"It’s a really special moment for me," Alcaraz said. "I was a little bit down after the injury, so I had to recover in those four months the confidence and the rhythm.

"Coming back for my first tournament of 2023 and making the final is so special for me."

Alcaraz has won all three matches at the Argentina Open, dropping only one set against Laslo Djere in his return match in the second round.

Taylor Fritz beat countryman Mackenzie McDonald for a spot in the Delray Beach Open final in Florida, fighting back from a break down in the second set to win 6-3 7-6 (8-6) and a secure a berth in his 10th career final.

Fritz, the top seed at Delray Beach, will take on Serbia's Miomir Kecmanovic in the decider after he won 7-6 (10-8) 3-6 6-2 over Moldova's Radu Albot.

Berrettini, Fritz and Rublev progress at Indian Wells

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.

Berrettini, Tsitsipas and Auger-Aliassime target 2022 ATP title hat-tricks

Former Wimbledon runner-up Berrettini beat American Mackenzie McDonald 3-6 7-6 (7-2) 6-3 at the hard court event, while Musetti came through 6-3 6-4 against Serbian Miomir Kecmanovic.

Providing Berrettini is healthy to participate in the final, the tournament looks set to deliver a crowd-pleasing trophy match, but it was touch and go whether the Rome native would get through the McDonald match.

"I don't even know how I did it," Berrettini said. "I wasn't feeling very good. I asked for the physio because my foot was hurting. It happened so many times in my career that I had to fight through so many things, not just thinking about the tennis ball."

He added, quoted by the ATP: "I didn't want to retire. My team told me, 'I think you should stop'. But I tried and I found a way."

Berrettini and Musetti have never gone head-to-head before. Berrettini has won two titles this year, both on grass, in Stuttgart and at London's Queen's Club, while 20-year-old Musetti scooped his maiden ATP title on clay in Hamburg.

At the European Open in Antwerp, Sunday's final will see American Sebastian Korda tackle Canadian Felix Auger-Aliassime, in a battle of two in-form players.

Korda was runner-up last week in Gijon, while Auger-Aliassime took the title in Florence, adding to his Rotterdam triumph from February.

Korda wrestled his way past a recently resurgent Dominic Thiem, scraping a 6-7 (4-7) 6-3 7-6 (7-4) victory, before Auger-Aliassime was given a mighty battle by veteran Frenchman Richard Gasquet, winning through in two tight sets, 7-6 (7-2) 7-6 (7-3) his margin.

Like Berrettini and Auger-Aliassime, Greece's Stefanos Tsitsipas has a third title of the year in his sights this weekend.

Tsitsipas swept through to the final of the Stockholm Open with a 6-2 6-2 win over Finland's Emil Ruusuvuori, setting up a clash with 19-year-old Danish player Holger Rune.

For Rune, there was no such straightforward path into the final as Alex de Minaur pushed him all the way, with the Australian eventually edged out 4-6 7-6 (7-1) 7-5 after two hours and 50 minutes.

Djokovic battles back again to secure Belgrade semi

The world number one had battled from a set down against Laslo Djere 24 hours earlier and was once more made to work hard for his win versus Miomir Kecmanovic. 

The seventh seed took the opener without facing a break point and led early in the second set too. 

But Kecmanovic could not hold off Djokovic, who recovered to win 4-6 6-3 6-3 and reach the last four for the fourth time in five campaigns in Belgrade. 

After two victories in two nights against Serbians for the two-time winner, Djokovic is on a 10-0 run in matches with his compatriots and 27-4 all-time. 

The 20-time grand slam champion also has a 36-6 record in Serbia and has particularly enjoyed the "strange" opportunity to face his countrymen in front of a home crowd. 

"It's a very strange feeling, sharing the court with your compatriots," he said. "Obviously the crowd was phenomenal for both players in yesterday's match and today's. 

"They're very rare occasions when I'm able to play at home and experience this atmosphere, so I'm trying to enjoy every single moment." 

Djokovic is the last Serbian remaining in the tournament, though, and takes on third seed Karen Khachanov – a winner against Thiago Monteiro – in the semis. 

There remain two quarter-finals to play on Friday, as Andrey Rublev faces Taro Daniel while Fabio Fognini welcomes the challenge of Oscar Otte. 

Meanwhile, there were only two matches completed at the Barcelona Open due to rain, but Ilya Ivashka ensured fans were rewarded for their patience as he took Stefanos Tsitsipas the distance. 

Ivashka eventually went down 6-1 4-6 6-2 to the top seed in a heavily delayed second-round contest. 

Djokovic cheered on Australia comeback, Auger-Aliassime and Rune among first round exits

Djokovic – who saw a three-year visa ban lifted in November – was playing with Vasek Pospisil in the doubles, and the duo lost 4-6 6-3 10-5 to Tomislav Brkic and Gonzalo Escobar on Monday, but the fans in attendance chanted "Novak" as they welcomed him back following his absence from last year's Australian Open.

The Serbian will face Constant Lestienne in the first round of the men's singles, but second seed Felix Auger-Aliassime is already out after he lost to Alexei Popyrin.

Auger-Aliassime struggled throughout as his Australian opponent, ranked 120th in the world, put in a crowd-pleasing performance to go through 6-4 7-6 (7-5).

Another young star, Holger Rune, is also out after the fifth seed was beaten 2-6 6-4 6-4 by Yoshihito Nishioka.

Quentin Halys set up a potential second-round clash with Djokovic after beating Jordan Thompson in straight sets, while Miomir Kecmanovic, Jack Draper, Roman Safiullin and Thanasi Kokkinakis all progressed.

It was also a bad day for seeds at the Maharashtra Open in Pune, with Alex Molcan beaten 6-2 6-4 by Laslo Djere and Jaume Munar losing 6-4 7-5 to Tallon Griekspoor.

Dutchman Griekspoor will now play Marco Cecchinato after the Italian overcame Nikoloz Basilashvili, and Roberto Carballes Baena set up a last-16 clash against top seed Marin Cilic by defeating fellow Spaniard Bernabe Zapata Miralles.

Filip Krajinovic did make it through a tussle with home favourite Sumit Nagal to set up a meeting with Michael Mmoh, while Benjamin Bonzi will face third seed Emil Ruusuvuori after beating Tseng Chun-hsin.

Fritz fends off Kecmanovic in Delray Beach Open decider

Fritz, 25, came into the tournament sitting at a career-best rank of seventh, and he did not lose his first set in Delray Beach until the final.

The top seed, Fritz was nearly perfect in the opening set, hitting 15 winners with only one unforced error and taking 72 per cent (28-of-39) of the total points. Kecmanovic did not hit a single winner in the set.

The 23-year-old Serbian showed far more fight in the second, and after saving all three of Fritz's break-point opportunities – including one match point – Kecmanovic capitalised on his one and only break-point chance of the match to force a third set.

But the mistakes crept back into the underdog's game, shooting himself in the foot with a pair of double faults and more unforced errors than winners.

Fritz took full advantage, securing two breaks down the stretch to run away with the victory and his first title of 2023.

After winning just one of his first six finals on the ATP Tour, Fritz has now won the past four finals he has reached.

Garin stunned by Rune at Serbia Open, Musetti progresses in Barcelona

The Chilean fifth seed, who was the highest-ranked player in action, is regarded as one of the ATP Tour's best on clay but hardly got a look-in as 18-year-old Rune emerged with an impressive 6-3 6-1 win.

Rune has risen to a career-high 72 in the ATP rankings and showed every sign that he will continue to climb over the season as he produced an aggressive performance that saw him take six of 17 break points.

Playing in only his fifth ATP Tour match on clay, Rune needed just an hour and 25 minutes to see off Garin – the winner of five tour-level titles on the surface – and set up a second-round clash with either Dusan Lajovic or Taro Daniel.

Sixth and seventh seeds Fabio Fognini and Miomir Kecmanovic avoided similar shocks, though their respective wins were wildly different.

Kecmanovic crushed veteran Richard Gasquet 6-0 6-3, while Fognini was forced to overturn a one-set deficit in his defeat of fellow Italian Marco Cecchinato 6-7 (5-7) 6-2 6-2.

No seeds were in action at the Barcelona Open, but Italian prospect Lorenzo Musetti enjoyed a hard-fought 7-5 7-5 defeat of Argentina's Sebastian Baez to seal his spot in the second round.

The 20-year-old is now 5-2 for the clay season and will go up against Dan Evans next. Joining Musetti in progressing is another promising youngster in Brandon Nakashima, who beat Nicolas Alvarez Varona 7-6 (8-6) 6-3 to tee up a clash with number two seed Casper Ruud.

Mackenzie McDonald, Elias Ymer, Kwon Soon-woo and Federico Coria were among the other victors, while retiring 2004 champion Tommy Robredo bowed out with a 6-1 6-1 loss to Bernabe Zapata Miralles.

Jack Draper suffers opening-rubber defeat as Serbia seize control at Davis Cup

Draper’s 7-6 (2) 7-6 (6) defeat left Cameron Norrie needing to hand Novak Djokovic just his seventh loss of the season to send the tie to a deciding doubles.

Serbia sprang a surprise by picking Kecmanovic, ranked five places above Draper at 55 in the world, ahead of their number two Laslo Djere, but the 24-year-old fully justified the decision with an impressive display.

Twenty-one-year-old Draper was unable to impose his big game on the match and came out on the wrong end of two tie-breaks in a contest lasting two hours and two minutes.

The tie did not get under way until 6.10pm, more than two hours later than billed, because of the over-running first match of the day between Italy and the Netherlands.

Around 5,000 British fans, including Dan Evans, who was forced out of the event through injury after playing the leading role in qualification, made up the majority of a virtually full crowd at the Palacio de Deportes Martin Carpena.

The International Tennis Federation’s decision to move away from the traditional home-and-away format and to a World Cup-style event has been unpopular with players and fans, but this was the sort of occasion they would have envisaged.

It was a huge moment for Draper, who only played his first match in the competition in September in Manchester and now found British hopes depending on him given the presence of Djokovic in the second rubber.

He could draw on better recent form than Kecmanovic, having reached his first ATP Tour final in Sofia earlier this month while the Serbian had lost his last four matches, and also won their only previous meeting on clay in May.

But Kecmanovic is a quality player who was ranked in the top 30 at the start of the year and, despite three aces in his first service game from Draper, it was the Serbian who was the more impressive in the early stages.

Draper had to dig deep to save two break points in a long eighth game and then found himself facing two set points at 4-5, which he again fought off in gutsy fashion.

But two double faults cost him dearly in the tie-break and left him with a lot of work to do to turn the match around.

Neither man faced a break point in the second set, but again it was Kecmanovic who looked the more convincing on serve.

After losing five points in a row from 2-0 up in the tie-break, Draper did well to level at 5-5 and then save a match point with a volley that just caught the line, but a wayward forehand gave Kecmanovic a second chance and this time the British youngster netted a return.

Kovacevic upsets Kecmanovic in Seoul

American Kovacevic was only playing in the first round as a lucky loser in Seoul after he was beaten in the final round of qualifying, but he grasped his chance by winning 6-4 6-4.

The 24-year-old served 14 aces and broke the world number 32 three times to set up a second-round meeting with Christopher O'Connell or Tseng Chun-hsin.

Radu Albot got the better of Hiroki Moriya in his first appearance in Seoul, while Jaume Munar progressed when Yosuke Watanuki retired early in their match due to an ankle injury.

Kaichi Uchida came out on top in the final match of the day, consigning Hong Seong-chan to a 6-4 6-2 defeat.

Medvedev cruises into Los Cabos semi-final, Evans upsets Fritz in Washington

The world number one gave Berankis no avenues into the match, winning 48 per cent (27-of-56) of his total return points, while also converting 88 per cent (21-of-24) of his own successful first serves into points.

Medvedev will meet Serbia's Miomir Kecmanovic in the semi-final after he pulled off an impressive 6-2 6-4 victory against American Brandon Nakashima.

Kecmanovic's ability to serve his way out of trouble was the deciding factor, saving four of five break-point opportunities, while Nakashima could only save six out of 10.

Canada's Felix Auger-Aliassime booked his spot in the second semi-final after defeating America's Steve Johnson 6-4 7-6 (7-3).

The 22-year-old winner – who now sits ninth in the world rankings – served up 17 aces in the contest, while Johnson, who is usually known for his serve, could only muster four.

Cameron Norrie was a straights-sets winner over Radu Albot, although he needed a second-set tie-break to get the job done in a 6-3 7-6 (7-4) triumph.

Meanwhile, Norrie's British compatriot Daniel Evans won a war of attrition against American Taylor Fritz at the Washington Open, pulling ahead 3-6 7-6 (8-6) 4-1 before the heavy favourite retired due to the oppressive conditions.

With rising temperatures, combined with spots of rain, the humidity threatened to claim a number of scalps as multiple players in Thursday's action took extended medical timeouts, before a serious downpour halted the rest of play.

The only other matches to reach their conclusion were Yoshihito Nishioka's 7-6 (7-2) 7-6 (7-1) win against Karen Khachanov, and a 6-3 6-7 (3-7) 6-4 triumph for Sweden's Mikael Ymer against Finland's Emil Ruusuvuori.

When play resumes, Nick Kyrgios will look to finish off Reilly Opelka after reaching the rain with a 7-6 (7-1) 2-1 lead, and Grigor Dimitrov won his first set 6-4 against Sebastian Korda.

Botic van de Zandschulp was the beneficiary of the break against Frances Tiafoe, winning the first set 6-4 before slowing down in a big way to drop the second 6-2, but he will get a chance to recharge his batteries before the decider.

Medvedev cruises past Murray in Miami, Tsitsipas pushed again

Medvedev must reach the semi-finals in order to retake the top spot in the ATP rankings from Novak Djokovic in April, and he got off to a positive start in Miami, not facing a single break point in his 90-minute win.

"On the days when you serve good, your opponent doesn't have this freedom to return, it helps you," Medvedev said post-match.

"[In the] second set, the scoreline was easier, it was much tougher in the beginning, but when your opponent knows you're probably going to get some aces and it's not going to be easy for him to return, he gets pressure on his serve and many times that is what happens in close matches."

Medvedev will face Pedro Martinez, who defeated Cristian Garin 7-6 (6-2) 6-2.

Reigning Miami champion Hubert Hurkacz got his title defence off to a good start with a 7-6 (7-5) 6-2 victory over Arthur Rinderknech.

Following defeats for Murray and John Isner, the Polish world number 10 is the only former champion left in the draw.

A number of men's seeds were beaten in their second-round matches on Saturday, however, including Canadian duo Felix Auger-Aliassime and Denis Shapovalov.

Miomir Kecmanovic continued his good run of recent form, defeating Auger-Aliassime in straight sets 6-4 6-2, while South African Lloyd Harris beat Shapovalov 6-4 6-3.

For his third consecutive ATP 1000 match, meanwhile, Stefanos Tsitsipas was pushed to three sets by an unseeded American.

After some entertaining hitting, with both looking to finish points early, the Greek third seed claimed four straight breaks of serve to eventually defeat Jack Wolf 6-4 6-7 (5-7) 6-1.

Medvedev moves into French Open third round after Kecmanovic retires injured

The former US Open champion prevailed in just 55 minutes at 6-1 5-0 ahead on Court Suzanne-Lenglen, when his opponent was unable to continue.

Medvedev has never progressed beyond the quarter-finals of the clay-court major, reaching the last eight in 2021, but has plenty of energy still in reserve after his premature win.

A runner-up at the Australian Open and Indian Wells this season, the fifth seed was in dominant form throughout the contest, and will play either Mariano Navone or Tomas Machac in round three.

Data Debrief: Medvedev continues to make strides on clay

Medvedev has now won 36 career ATP matches on clay, with 50 per cent of those coming since the start of the 2023 season (18).

The fifth seed won 23 of his 27 points on first serve (85 per cent), while converting five of nine break points, and hitting 26 winners to just six unforced errors.

Medvedev unfazed by Hurkacz defeat, as Alcaraz progresses in Miami

Medvedev had to deal with dizziness and fatigue during the match, taking a medical timeout against the defending champion in Miami, and was disappointed he was not able to produce his best tennis.

The defeat means the 25-year-old will stay behind Novak Djokovic, who has not played on the ATP Tour since losing to Jiri Vesely back in the quarter-finals in Dubai.

Heading into the clay season, the Russian world number two is buoyant after a 4-2 record across Acapulco and Indian Wells.

"I'm kind of happy about the tournament in Miami in a way of tennis… I managed in Miami to find just a little spark to make it work," Medvedev said post-match.

"Today was not enough, but I'm happy that I saw that I'm able to do it. I'm in the right direction, so it's good."

Hurkacz will face Carlos Alcaraz, who made his second ATP 1000 semi-final after a thrilling 6-7 (5-7) 6-3 7-6 (7-5) victory against Miomir Kecmanovic.

Both Alcaraz and Kecmanovic exhibited extraordinary court coverage in a match-up between two of the more adept returners of serve on the tour, but the 18-year-old Spaniard could simply find a higher gear as points progressed.

Alcaraz played some inspired tennis to break back in the seventh game in the opening set, shifting Kecmanovic around the court to set up a stunning cross-court backhand pass for break point, before stepping in on the second serve to restore parity.

Despite Kecmanovic holding to love in his next two service games, it did not put consequent pressure on his teenage opponent, who forced a tie-break. However, Kecmaovic clawed back from a mini-break to take a riveting opening set.

Hitting 52 winners for the match, the world number 16 pulled out his best tennis of the match in Kecmanovic's opening service game of the second set, coming up with a magnificent lob on the run to set up the break.

Saving break point while serving for the set, he held out to force a deciding third. Coming back from a mini-break in the third set tie-break, Alcaraz ended the match on fitting note, scrambling to the net to slice past Kecmanovic at the end of a frenetic rally.

Nadal grinds it out over Opelka, Berrettini shocked at Indian Wells

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.

Novak Djokovic and Serbia end Great Britain’s Davis Cup hopes in Malaga

Britain’s dramatic success against France in Manchester in September had sent them through to the final eight event for the first time in the revamped format.

But they fell at the first hurdle, with Miomir Kecmanovic defeating Jack Draper 7-6 (2) 7-6 (6) before Djokovic comfortably saw off Cameron Norrie 6-4 6-4 to send a jubilant Serbia through to a semi-final against Italy on Saturday.

Given the presence of Djokovic, who cemented his position at the top of the sport by winning a seventh ATP Finals title on Sunday, Britain’s hopes depended on Draper winning the first rubber.

The tie did not get under way until 6.10pm, more than two hours later than billed, because of the over-running first match of the day between Italy and the Netherlands.

There were around 5,000 British fans in a near-capacity crowd, giving the event the sort of authentic Davis Cup feel that has so often been missing since the switch from the home-and-away format.

Among those sat in the stands at the Palacio de Deportes Martin Carpena was Dan Evans, who had hoped to build on his brilliant performances in Manchester before a calf injury prematurely ended his season.

But even the British number two would have had his work cut out against an inspired Kecmanovic, who was chosen ahead of the higher-ranked Laslo Djere and fully justified the decision.

Draper had the better form coming in having reached his first ATP Tour final this month and had beaten Kecmanovic – ranked five places higher at 55 – earlier this year, but the Serbian was dominant on serve and edged two tie-breaks.

Draper hung on during the first set, saving two break points at 3-4 and then two set points at 4-5 with some gutsy play only to double fault twice in the tie-break.

His chance came when he recovered from 2-5 to level at 5-5 in the second tie-break but, despite saving a match point, he could not force a decider.

It was only the 21-year-old’s second Davis Cup rubber and he admitted knowing Djokovic was looming added to the nerves he felt.

“That’s seemingly a must-win match for me,” said Draper. “It’s definitely a tough challenge to go out there knowing that there is a lot more pressure on me to win the match.

“That’s the kind of pressure that, if I want to be a top player, I have to cope with and have to perform under. It’s tough not to get the win today. I gave it all I had mentally. I didn’t do a few things as well as I wanted to, but he played a great match.”

Djokovic had lost only six of his 61 previous matches this season, with just one defeat since the Wimbledon final, while his Davis Cup record is utterly formidable.

It is 12 years since he lost a singles match in the competition, and even that was by retirement, with now 21 straight wins and only four sets dropped.

Norrie had managed only a single set in three previous meetings and has endured a miserable run since the clay-court swing back in the spring, but he was captain Leon Smith’s only option once Andy Murray pulled out with a minor shoulder injury.

He did not put in a bad performance by any means, but was fire-fighting from the moment he was broken at 2-2 in the opening set, throwing everything he had at Djokovic to fight back from 0-40 in his next service game.

The Serbian lost just three points on serve in the first set – and only eight in the match – and blew kisses towards a vocal British fan who had been warned by the umpire after clinching it to love.

Norrie promptly dropped serve to start the second set before again hanging on grimly, this time saving five break points at 1-3, but Djokovic was able to stay in his comfort zone through to the finish line.

While Serbia are a step closer to the trophy, Britain must start again in February in the qualifiers – barring an unlikely wild card through to September’s group stage.

Novak Djokovic left to rue ‘bitter’ end to season as Serbia beaten in Davis Cup

The world number one suffered an unwanted career first when he failed to convert three consecutive match points in a pulsating 6-2 2-6 7-5 singles loss – his first in the competition in 22 matches and 12 years.

Serbia had led 1-0 in the semi-final in Malaga thanks to Miomir Kecmanovic’s win over Lorenzo Musetti but Djokovic’s defeat sent the tie to a deciding doubles contest.

Djokovic and Sinner lined up on opposite sides of the net for the fourth time in less than two weeks alongside Kecmanovic and Lorenzo Sonego respectively, and it was the Italian duo who clinched a 6-3 6-4 win to send their country through to a clash with Australia for the title on Sunday.

Djokovic had hoped to crown the season in which he became the most successful man in tennis history with a second Davis Cup title, and he made no attempt to hide his disappointment.

“Congratulations to Italy for qualifying for the finals,” he said. “They deserved it. They played really well, particularly Jannik, in singles against me and then doubles, as well. He barely missed a ball the entire match.

“For me personally it’s a huge disappointment, because I take the responsibility, obviously having three match points, being so close to winning it. It’s unfortunate really. This is sport. When you lose for your country, the bitter feeling is even greater.”

After Kecmanovic had backed up his fine showing against Britain’s Jack Draper by coming from a set down to defeat Musetti 6-7 (7) 6-2 6-1, the stage seemed set for Djokovic to send Serbia through to the final.

The confidence Sinner had gained from his group stage victory over Djokovic at the ATP Finals was negated by a convincing loss in the final but the world number one looked fatigued, perhaps more mentally than physically, during the first set.

Both men had headed straight from Turin to Malaga but Sinner is 14 years younger than his rival and he took full advantage of some uncharacteristic errors to reel off five games in a row.

It was another excellent atmosphere at the Palacio de Deportes Martin Carpena, befitting the sort of marquee clash that Davis Cup has not seen enough of over the last decade and more.

Djokovic showed more positive energy at the start of the second set and was pushing for a break throughout the decider.

But Sinner refused to buckle, saving break points in two separate games prior to his remarkable renaissance at 4-5, when he won five points in a row from 0-40.

In a reminder that even the very best are not immune to pressure, the Serbian was then broken himself and Sinner served out a stunning victory.

Djokovic’s record in doubles is poor and, in a contest that made up for in drama what it lacked in quality, the Italian duo claimed a deserved victory to crown Sinner’s special day.

The world number one, who again became involved with the crowd, this time conducting along to Italian jeers, refused to blame fatigue, saying: “I don’t want to talk about it because it’s going to sound like an excuse.

“Obviously this is a tough one to swallow. I was really trying to hype myself and encourage myself for this week. Throughout the entire season, my thoughts were this week with my Davis Cup team. I tried to contribute. I did in the first tie, but today it wasn’t meant to be.”

Rublev, Fritz secure semi-final berths at Indian Wells

Dimitrov had only faced two break points for the tournament until this quarter-final, and Rublev capitalised when his opponent’s serve evaded him. Rublev was returning with particular focus, getting 85 per cent of points back across the court on Dimitrov's first serve alone.

Rublev broke in the fifth game of the first set on the back of two double faults, but Dimitrov secured one of his own with a trademark backhand pass. The 24-year-old Russian answered right back to regain breathing room and close out a tight first set.

Securing the break in the third game of the second, that consistent pressure on Dimitrov's serve again forced two double faults in the fifth game. From there at 4-1, Rublev saw the finish line.

The win was the seventh seed’s 13th in a row, adding Indian Wells to semi-final appearances at Miami, Monte Carlo and Cincinnati. A win in the final would equal a career-high 15 matches in a row undefeated.

"I think I played really well. In the beginning, it was more about who will be the first to dictate and play more aggressive, because both of us like to dictate with our forehand," Rublev said afterwards.

"The return [of serve] was one of the most important things. If you can bring as many returns as possible [into the court], and then here with these conditions, in some moments it's tough to serve."

In Friday's other quarter-final, Taylor Fritz did it tough against the unseeded Serbian Miomir Kecmanovic, winning 7-6 (7-5) 3-6 6-1.

While Kecmanovic was content playing defence and grinding from the baseline, Fritz was the more active and it was most apparent at 5-5 in the first set.

Down 0-30, Fritz stood and delivered from the middle of the baseline with a booming forehand, before securing a critical hold.

The difference in tactics showed in the eventual winner differential, with Fritz's 35 in comparison to Kecmanovic's 15. Despite Fritz's relatively low unforced error count, he still gifted Kecmanovic the second set, serving three consecutive double faults to surrender the break at 3-4.

He regrouped and reeled off the opening five games of the third set, setting up his semi-final with Rublev. The other semi-final will see Rafael Nadal and Carlos Alcaraz meet in an all-Spanish duel.

Rune shocks Zverev at BMW Open

The world number three and top seed had no answer to an impressive performance from Rune, with the young Dane ultimately easing to a 6-3 6-2 victory on Wednesday.

Rune set the tempo early on, moving Zverev around the court with plenty of drop shots and heading into a 4-2 lead, before saving two break points on his way to clinching the first set.

An early break in the second then seemed to give the 18-year-old the confidence to see out his first career victory against a top 10 opponent.

"It was a difficult match from the beginning," said Rune on-court after the win. "He's in the top three in the world and has been playing some unbelievable tennis, especially in the past year winning so many big titles.

"I have a lot of respect for him, and I obviously didn't expect to win in two sets, and with a score like this. But it was a really hard match, we played a lot of rallies and I'm really happy about my performance today."

Rune will play Emil Ruusuvuori in the quarter-finals after the Finn beat Maxime Cressy 6-3 6-3.

Elsewhere, fourth seed Nikoloz Basilashvili came from behind to overcome Ilya Ivashka 3-6 6-2 6-4, and will face Miomir Kecmanovic in the last eight after the seventh seed beat Daniel Altmaier 6-2 6-4.

There were also three round of 32 matches on Wednesday, with eighth seed Botic van de Zandschulp, Egor Gerasimov and Alejandro Tabilo all through to the last 16 in Munich.

Over at the Estoril Open, Alejandro Davidovich Fokina will play Frances Tiafoe in the quarter-finals after both advanced in Portugal.

Fourth seed Davidovich Fokina beat fellow Spaniard Bernabe Zapata Miralles 6-3 7-6 (7-5) while fifth seed Tiafoe got the better of Nuno Borges 7-6 (7-4) 4-6 6-0.

Fernando Verdasco is also through after a 6-2 6-3 win against Pablo Cuevas, and he will play fellow Spaniard and sixth seed Albert Ramos-Vinolas, who came from a set down against Kwon Soon-woo, 5-7 6-1 6-2.

Ruud downs Kecmanovic to clinch Estoril title, Carballes Baena victorious in Marrakesh

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.