Alex de Minaur was again stunned by Marcos Giron as the third seed crashed out of the Sofia Open in the second round. 

Following his success over De Minaur at the Moselle Open last week, Giron beat the world number 26 once more as he battled to a 7-6 (7-5) 7-6 (7-2) victory in two hours. 

The unseeded American, appearing for the first time in Sofia, rallied from a break down in the second set to reach an ATP Tour quarter-final - where he will meet John Millman - for the fourth time this season. 

Millman, who is seeded eighth, lost the first set against qualifier Illya Marchenko but recovered well to comfortably triumph 5-7 7-6 (7-0) 6-3. 

However, it was far more straightforward for the other favourites, with top seed Jannik Sinner avoiding a second-set blip to defeat Egor Gerasimov 6-2 7-6 (7-3) and Gael Monfils getting a walkover against Ilya Ivashka. 

Number five seed Filip Krajinovic coasted past fellow Serbian Laslo Djere 6-3 6-0 in just over an hour to set up a quarter-final tie with Kamil Majchrzak. 

In Thursday's other match, world number 56 James Duckworth smashed Benoit Paire 6-4 6-4 in just an hour and 15 minutes to collect his 11th win in his past 12 outings. 

Duckworth, who reached his first ATP Tour final in Nur-Sultan last week, will now challenge defending champion Sinner in the next round. 

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.

Casper Ruud survived a scare as he progressed to the Generali Open semi-finals with a 3-6 7-6 (7-5) 6-1 victory over Mikael Ymer.

World number 14 Ruud is targeting a third successive ATP title, having also captured the Swedish Open and Swiss Open earlier this month.

It has been a timely return to form for the Norwegian, who suffered a shock defeat to Australia's Jordan Thompson at Wimbledon at the end of June.

Although he was in danger of seeing his nine-match winning streak come to an end in Kitzbuhel, after losing the opening set against Swedish opponent Ymer.

Ruud, who also triumphed at the Geneva Open in May, was then taken to a tie-break in the second ser by the world number 99, but held his nerve to tee up a decider.

It was one-way traffic from there with the 22-year-old dominating play to set up a last-four clash with Arthur Rinderknech, who hit five aces as he overcame third seed Filip Krajinovic 6-4 6-1.

Meanwhile, Daniel Altmaier's place in the semi-finals was secured with a 6-1 6-7 (5-7) 6-3 win over Gianluca Mager.

The world number 135, who reached the fourth round of last year's French Open, will play Pedro Martinez in the semi-finals after the Spaniard saw off Jozef Kovalik 6-2 6-2.

World number 16 Roberto Bautista Agut crashed out in the second round as the other favourites for the Generali Open battled through.

Bautista Agut lost the first set to Spanish compatriot Pablo Martinez in Kitzbuhel, Austria, and could not complete a comeback despite forcing a decider as he lost 6-4 6-7 (5-7) 7-5.

Top seed Casper Ruud, who won last week in Gstaad to claim his third ATP Tour crown of 2021 and fourth in total, came from 4-2 down in the first set to win 7-5 5-7 6-4 against Mario Vilella Martinez.

Third seed Filip Krajinovic survived a second-set scare to beat Carlos Taberner 6-3 2-6 6-4.

Arthur Rinderknech, who dispatched of fifth seed Federico Delbonis on Tuesday, awaits Krajinovic in the next round.

The other clash on Wednesday saw Sweden's Mikael Ymer cruise past home favourite Alexander Erler 6-2 6-3 to secure a quarter-final berth.

Ymer will now face the thankless task of challenging 22-year-old Ruud for a spot in the semi-finals.

Pablo Carreno Busta beat Filip Krajinovic in the final of the Hamburg European Open to lift his first ATP 500 trophy.

Spanish second seed Carreno Busta wrapped up a convincing 6-2 6-4 win over Krajinovic of Serbia in one hour and 23 minutes.

Krajinovic, who beat Stefanos Tsitsipas in the quarter-finals, had no answer to Carreno Busta's serve as he won 81 per cent (21/26) of his first-service points.

Carreno Busta broke Krajinovic's serve twice in the first set before he served out. 

Krajinovic showed more fight in the second set, but he was unable to create a break chance, and when he offered one to Carreno Busta his opponent seized it.

The victory gave world number 13 Carreno Busta, who did not drop a set in the tournament, his 17th win on clay this season.

 

Filip Krajinovic will take on Pablo Carreno Busta in the Hamburg European Open final on Sunday.

A memorable week for Krajinovic continued as he saw off fellow Serbian Laslo Djere 6-4 6-2 in his semi-final.

Sixth seed Krajinovic defeated Stefanos Tsitsipas in the quarter-finals and ensured he followed up on that surprise victory with a dominant display against Djere on Saturday.

The victor committed only seven unforced errors in the match, while conceding just two break points in the contest.

Second seed Carreno Busta has not dropped a set all week and kept that run going with a 7-6 (7-2) 6-3 win over Federico Delbonis.

Carreno Busta needed just under two hours to see off a battling Delbonis, with neither player offering up a single break point in a first set that went the distance.

The Spaniard won five straight points to take the tie-break and continued that momentum into the second set when he broke Delbonis twice.

Neither Carreno Busta nor Krajinovic has ever won a tournament at ATP 500 level or above.

Carreno Busta has five career titles, but all of those are at ATP 250 level, losing to Dominic Thiem in his only showpiece appearance at this level at the Rio Open back in 2017.

Krajinovic, meanwhile, has lost all three of the career finals he has reached.

"I enjoy playing here, I feel comfortable here," Carreno Busta said. "It is my most important match this year on Sunday - I need to be really focused until the end.

"[Delbonis] is a really tough player and my level was very good. I probably played better in the second set, but I continued fighting all the time."

At the Nordea Open in Bastad, Sweden, top seed Casper Ruud was comfortable as he defeated Roberto Carballes Baena 6-1 6-4 to earn a place in the final.

Ruud needed just 79 minutes to do the job, breaking Carballes Baena on five occasions. 

He has only played two matches – both comfortable wins – to reach the final after a walkover against Henri Laaksonen in the quarters.

Rising star Ruud will bid for his second ATP title of the year and the third of his career against Federico Coria on Sunday.

Coria also had a comfortable last-four tie, seeing off Germany's Yannick Hanfmann 6-2 6 -1, with the win meaning the 29-year-old reached his maiden career tour final.

"I am very happy - it is my first final," said world number 77 Coria, who beat second seed Cristian Garin in the last eight.

"I played the best tennis of my life in this match. It is amazing here in Bastad, it is beautiful."

Stefanos Tsitsipas will head into the Tokyo Olympics on the back of a disappointing quarter-final exit at the Hamburg European Open.

The world number four made a fast start to his match against Filip Krajinovic, winning the opening five games, but fell away to lose in three sets after an hour and 59 minutes.

Tsitsipas is due to represent Greece at the behind-closed-doors Games in Japan, where he will be among the medal favourites.

His racket bizarrely fell apart in the second set against Krajinovic, with Tsitsipas left clutching just the handle as the head broke off when he attempted a backhand.

Despite reaching for a replacement racket, Tsitsipas could not get the better of his 44th-ranked Serbian opponent.

Krajinovic said, according to the ATP website: "He started really well, really aggressively. I could not find my game, could not find my serve, he was overpowering me. But at the end of the first set, I started to feel better, I was going for my shots.

"It paid off in the end. I am happy to beat Tsitsipas, he is an amazing player. I always play well here, and I hope I keep playing well here."

Krajinovic advances to take on a fellow Serbian, Laslo Djere, in the semi-finals, after Djere swept to a 6-2 6-2 win over Georgian Nikoloz Basilashvili.

Spanish second seed Pablo Carreno Busta prevented a third Serbian reaching the final four, beating Dusan Lajovic 7-6 (7-4) 6-3, and he will face Federico Delbonis on Saturday.

At the Nordea Open in Bastad, Sweden, top seed Casper Ruud had his path to the semi-finals smoothed by the withdrawal of scheduled opponent Henri Laaksonen due to injury.

That walkover means Norwegian Ruud will next tackle Roberto Carballes Baena, who beat Slovakian Norbert Gombos 6-4 6-2.

Chilean second seed Cristian Garin bowed out, beaten 6-4 4-6 6-2 by Argentinian Federico Coria. Coria's semi-final opponent will be Germany's Yannick Hanfmann, a 6-4 6-3 victor over French qualifier Arthur Rinderknech.

Jan-Lennard Struff and Filip Krajinovic had contrasting routes into the BMW Open quarter-finals on Thursday.

Home favourite Struff made it to the last eight of the clay-court tournament for the fourth time in his career with a 7-6 (7-3) 6-7 (0-7) 6-2 triumph over German countryman Dominik Koepfer, who had little to celebrate on his 27th birthday in Munich.

Struff recovered from 4-2 down to take the first set and racked up four straight games to seal the deciding set. He served 11 aces and staved off five break points in a match lasting two hours and 39 minutes.

"I am very, very happy that I turned around the first set," seventh seed Struff said in his on-court interview. 

"I played a not good second-set tie-break. Before [that] the set was okay, but I couldn't lock into his service games that much.

"I am very happy that I broke him I the third set and I am very happy to be through. Dominik is a good guy and a very good player."

Fourth seed Krajinovic stands in the way of Struff and a last-four berth, with the Serbian handed a walkover after last-16 opponent Yannick Hanfmann pulled out with a neck injury.

Nikoloz Basilashvili, seeded fifth, defeated Daniel Elahi Galan 6-4 6-2 to set up a last-eight clash with lucky loser Norbert Gombos, who overcame Federico Coria 6-4 6-1.

At the Estoril Open there was a battle between music collaborators as top seed Denis Shapovalov faced off against Corentin Moutet.

The duo were welcomed onto the court by the track 'Drip', which they released together last year.

On the court, it was Frenchman Moutet who managed to snare an upset victory in a 6-4 2-6 6-4 triumph against the Canadian, to score a second top-20 win of the year.

"It was a very close match," Moutet said. "I'm lucky that I won at the end. A few points decided the winner."

Next up is Albert Ramos-Vinolas, who defeated Pierre-Hugues Herbert 6-2 7-6 (7-3).

Cameron Norrie outlasted wildcard Pedro Martinez 4-6 7-6 (7-1) 7-5 to book a quarter-final against second seed Cristian Garin, who never took to the court as opponent Richard Gasquet withdrew with a left adductor problem.

Kei Nishikori's comeback surprised the former world number four, who survived a major scare to advance at the Barcelona Open.

Nishikori trailed 6-4 4-2 and was forced to break serve as Guido Pella attempted to close out the match in the second set, before sensationally rallying to a 4-6 7-6 (7-4) 6-2 win on Monday.

A two-time champion at the ATP 500 tournament on the Barcelona clay, Nishikori broke serve on three occasions in the final set en route to the second round.

"He had the match today at 6-5, serving [for the match]," said Nishikori. "He was much better in the first and second [sets] and 3-0 up in the tie-break. I don't know how I fought through. [In the] third set, I was playing much better.

"I was making so many unforced errors in the first and second [sets]. Maybe he got a little bit tired and I was playing strong in the third set. I want to take that to the next round… The way I fought today and the way I played in the third set was good."

Next up for 2014 US Open finalist Nishikori is 13th seed Cristian Garin.

Ilya Ivashka topped Tallon Griekspoor 6-3 6-1 and the qualifier's reward is a showdown with top seed and 20-time grand slam champion Rafael Nadal.

Cameron Norrie, Pablo Andujar, Jeremy Chardy, Pierre-Hugues Herbert, Jaume Munar, Federico Gaio, Egor Gerasimov and Bernabe Zapata Miralles all advanced to the last 32.

At the Serbia Open, seeds Filip Krajinovic and John Millman booked their spots in the round of 16.

With the ATP 250 tournament being staged for the first time since 2012 and headlined by world number one Novak Djokovic, Serbian fifth seed Krajinovic overcame Stefano Travaglia 7-5 5-7 6-3 in a Belgrade rollercoaster.

Millman – the Australian seventh seed – took down local wildcard Danilo Petrovic 7-5 6-4 as Marco Cecchinato and Nikola Milojevic won through.

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