Alexander Zverev survived and Rafael Nadal cruised as four top-10 seeds incredibly suffered losses in the US Open first round on Tuesday.

Zverev looked like potentially joining the list of casualties before edging past Radu Albot in five sets at Flushing Meadows.

Nadal, meanwhile, never looked in trouble as he retained his perfect record in the opening round in New York.

However, top-10 seeds did fall as Dominic Thiem, Stefanos Tsitsipas, Roberto Bautista Agut and Karen Khachanov made first-round exits.

 

ZVEREV EDGES THROUGH

A two-time French Open quarter-finalist, Zverev's record at grand slams has been questioned and it seemed set to be a talking point again.

But, the German sixth seed managed to get past Albot 6-1 6-3 3-6 4-6 6-2 after three hours, 10 minutes.

Zverev has never been beyond the third round at the year's final major and while the draw opened up on Tuesday, he faces a tough second-round match.

The 22-year-old will meet Frances Tiafoe, who led Ivo Karlovic 6-2 6-3 1-2 when the Croatian retired.

 

NADAL UNTROUBLED

Nadal, an 18-time grand slam champion, eased past John Millman 6-3 6-2 6-2 to improve to 15-0 in the first round at the US Open.

The Spaniard was relentless and consistent, eventually converting five of 15 break points in a comfortable win.

Nadal will face another Australian, Thanasi Kokkinakis, after the 23-year-old claimed his first main-draw win at a major since 2015 by beating Ilya Ivashka 6-3 7-6 (10-8) 6-7 (4-7) 6-2.

SEEDS FALL

The fourth-seeded Thiem was not at full fitness as the Austrian bowed out to Thomas Fabbiano 6-4 3-6 6-3 6-2.

Thiem and Tsitsipas made first-round exits at Wimbledon and the US Open, the Greek going down to another young star in Andrey Rublev 6-4 6-7 (5-7) 7-6 (9-7) 7-5.

Khachanov and Bautista Agut, the ninth and 10th seeds respectively, suffered shock losses.

Vasek Pospisil upset Khachanov 4-6 7-5 7-5 4-6 6-3, while Mikhail Kukushkin beat Bautista Agut 3-6 6-1 6-4 3-6 6-3.

Meanwhile, 2014 champion Marin Cilic progressed, Jo-Wilfried Tsonga was beaten and Nick Kyrgios advanced in straight sets.

Flushing Meadows was abuzz with excitement at the news Serena Williams and Maria Sharapova will meet in round one of the US Open.

Thursday's draw threw up an absolute humdinger of a tie between two of the greatest and most recognisable tennis stars of all time.

But there are plenty of other eye-catching matches in the first round of the final grand slam of 2019.

Below we have picked out six of the best to watch in New York.


SERENA WILLIAMS V MARIA SHARAPOVA

Undoubtedly the stand-out tie in the entire draw. There is little love lost between the two long-term foes, but the rivalry has been extremely one-sided. Sharapova's last prevailed against Williams way back in 2004 and, while the two have never faced off at the US Open, the Russian will need to roll back the years to end the drought.

ARYNA SABALENKA v VICTORIA AZARENKA

Sabalenka can be forgiven for cursing her luck at landing a daunting first-round tie with Belarus compatriot Azarenka, who she has never met in a competitive match. In a year that has seen her reach a career-high ranking of nine, a position she currently holds, a meeting with the former world number one straight out of the gate is not what she would have wanted as she aims to go beyond round four of a slam for the first time.

ALISON RISKE v GARBINE MUGURUZA

Two-time slam winner Muguruza faces a Riske-y tie in the opening round. The 29-year-old Riske has been consistently in the top 50 over the past six years and won the pair's past meeting in Tokyo in 2018.

RAFAEL NADAL v JOHN MILLMAN

On the face of it, this looks a complete mismatch, particularly as Nadal won their only competitive meeting at Wimbledon in 2017. But Australian Millman caused a mammoth upset at Flushing Meadows 12 months ago when he defeated Roger Federer to make the quarter-finals – his best result at a grand slam. He will be hoping for a repeat against three-time victor Nadal.

DENIS SHAPOVALOV v FELIX AUGER-ALIASSIME

In a nice coincidence, two of Canada's finest young stars meet in a repeat of a 2018 first-round tie. On that occasion, Shapovalov consoled his good friend with a big hug after Auger-Aliassime was forced to retire in the third set with the opening two having been shared. Both men have been tipped for big futures and this one could be a cracker.

STEFANOS TSITSIPAS v ANDREY RUBLEV

Tsitsipas' season has stalled after a brilliant start to 2019 that saw him reach the Australian Open semi-finals, where Nadal proved too big of a hurdle to overcome. A first-round defeat at Wimbledon was the precursor to a difficult hard-court warm-up for the Big Apple, which saw early exits in Montreal and Cincinnati – albeit he did reach the last four in Washington. Rublev was a quarter-finalist in Cincinnati, losing only to in-form Russian compatriot Daniil Medvedev, and as a fellow star of the 2018 Next Gen ATP Finals he will fancy his chances of an upset.

Stefanos Tsitsipas and Alexander Zverev were surprise second-round casualties at the Western & Southern Open, where Andrey Rublev set up a showdown with a seven-time champion.

Tsitsipas was sent packing following a shock defeat to Jan-Lennard Struff, while Zverev was surprisingly upstaged by Miomir Kecmanovic in three sets.

Fellow seed Kei Nishikori also exited the ATP Masters 1000 tournament but Rublev earned a meeting against Roger Federer.

 

STRUFF STRUTS HIS STUFF IN TSITSIPAS UPSET

Tsitsipas was tamed by Germany's Struff, who claimed a 6-4 6-7 (5-7) 7-6 (8-6) victory after two hours, 14 minutes in Cincinnati.

The Greek fifth seed managed to save three match points from 6-3 down in the third-set tie-break, but Struff was not to be denied his fifth win in his past 10 matches against top-10 opposition.

Struff's reward is a last-16 clash against Daniil Medvedev, who beat Benoit Paire 7-6 (7-2) 6-1.

 

ZVEREV TALLIES 20 DOUBLE FAULTS IN EXIT

World number six Zverev surrendered a lead as he went down 6-7 (4-7) 6-2 6-4 to Kecmanovic.

Zverev struggled after winning the opening set, recording a career-high 20 double faults to fall to 0-5 at the Masters event.

Kecmanovic, who reached his maiden Masters quarter-final in Indian Wells, will play 11th seed Roberto Bautista Agut for a spot in the last eight.

Spaniard Bautista Agut outlasted Frances Tiafoe 6-3 3-6 6-1. Meanwhile, sixth seed Nishikori lost to fellow Japanese Yoshihito Nishioka 7-6 (7-2) 6-4.

 

FEDERER AWAITS RUBLEV AFTER WAWRINKA WIN

From one Swiss to another. Russian Rublev dispatched Stan Wawrinka 6-4 6-4 to book a date with Federer.

Rublev saved all five break points against three-time grand slam champion Wawrinka.

The 21-year-old can now look forward to a first meeting with last year's runner-up Federer.

The likes of Karen Khachanov, David Goffin, Alex de Minaur and Richard Gasquet also progressed to the last 16.

Top seed and defending champion Rafael Nadal dug deep to make a winning start at the Rogers Cup, while Greek star Stefanos Tsitsipas suffered a shock defeat in Montreal.

Nadal – a four-time winner of the ATP Masters 1000 tournament – shook off rust to overcome Dan Evans in straight sets on Wednesday.

The outcome was not as good for fourth seed and last year's runner-up Tsitsipas, who was stunned by Hubert Hurkacz.

Tsitsipas was not the only seed to fall, with Kei Nishikori, Borna Coric, John Isner and Milos Raonic also departing.

 

NADAL ON TRACK FOR RECORD-EXTENDING MASTERS TITLE

World number two Nadal survived to beat Brit Evans 7-6 (8-6) 6-4 en route to the round of 16.

Nadal trailed 5-2 in the first-set tie-break but won six of the final seven points to take control and eventually the match.

Contesting his first match since losing to Roger Federer in the Wimbledon semi-finals, Nadal claimed his 35th Rogers Cup victory and 378th Masters win – tying the Swiss superstar on the all-time leaderboard.

Nadal, who has won a record 34 Masters crowns, will face Guido Pella for a spot in the quarter-finals after the Argentinian beat Radu Albot 6-3 2-6 7-6 (7-2).

 

TSITSIPAS OUSTED, CANADIAN PAIR FOLLOW

This time last year Tsitsipas reached the final, however, the 2018 runner-up was a surprise casualty on Wednesday following a 6-4 3-6 6-3 loss to Hurkacz.

Hurkacz saved nine of 10 break points against the world number five, who failed to convert any of his four chances in the third set.

Canadian duo Denis Shapovalov and Raonic, meanwhile, were sent packing.

Shapovalov was beaten 6-4 3-6 6-3 by second seed Dominic Thiem and Raonic retired due to a back injury, with countryman Felix Auger-Aliassime benefiting after the match was even at 6-3 3-6.

Thiem will meet 14th seed Marin Cilic, while sixth seed Karen Khachanov awaits Auger-Aliassime after topping Stan Wawrinka.

 

MURRAY'S DOUBLES CAMPAIGN ENDS

Andy Murray and Feliciano Lopez said goodbye in Montreal, upstaged by Roland Garros finalists Jeremy Chardy and Fabrice Martin.

A five-match winning streak was ended following a 2-6 6-3 10-8 loss in the second round of the tournament.

Nick Kyrgios put on a show as he prevailed against top seed Stefanos Tsitsipas in an entertaining ATP Citi Open semi-final.

Kyrgios saved a match point in a third-set tie-break to see off Greek star Tsitsipas 6-4 3-6 7-6 (9-7) in a Washington thriller on Saturday.

Much was expected from the blockbuster meeting and it lived up to the hype – Kyrgios producing underarm serves and even consulting a fan on match point as he booked a spot in the final.

Kyrgios, who led 5-1 in the final-set tie-break, even delivered shoes to Tsitsipas in the wildly entertaining contest in front of a sell-out crowd after the world number six struggled to find a spare pair.

Seeking his sixth career ATP title and second of the year, Kyrgios improved to 4-1 against top-10 players this season – the best record on tour in 2019.

Kyrgios, who won the Mexican Open in March, will face third seed Daniil Medvedev in Sunday's decider in the American capital.

Medvedev eased past lucky loser Peter Gojowczyk 6-2 6-2 as the Russian reached his eighth ATP final, with a fifth title up for grabs.

Stefanos Tsitsipas and Nick Kyrgios will meet in a blockbuster Citi Open semi-final after straight-sets wins on Friday.

Tsitsipas, the top seed at the ATP 500 event, ran away with a 7-5 6-0 victory over Frenchman Benoit Paire in their quarter-final.

The Greek star is into his seventh semi-final of the year and is set to rise into the world's top five after his run in Washington.

Tsitsipas' win over Paire was not without some controversy, with the 10th seed unhappy with the 20-year-old needing to change shoes early in the second set.

In what shapes as an entertaining last-four clash, Tsitsipas will face Kyrgios, with the pair having played doubles together in Washington.

Kyrgios' fine run continued with an impressive 6-3 6-3 victory over lucky loser Norbert Gombos.

In the other semi-final, Daniil Medvedev will take on Peter Gojowczyk.

Russian third seed Medvedev got past sixth seed Marin Cilic 6-4 7-6 (9-7) and lucky loser Gojowczyk upset Kyle Edmund 6-3 4-6 6-3.

In the doubles, brothers Andy and Jamie Murray bowed out in the quarter-finals.

Stefanos Tsitsipas advanced to the Citi Open quarter-finals and the in-form top seed was joined by Marin Cilic and Daniil Medvedev.

Tsitsipas was too good for Australian Jordan Thompson, prevailing 6-3 7-6 (7-4) to book a spot in the last eight on Thursday.

Greek star Tsitsipas saved a set point in the second set as he earned a clash with 10th seed Benoit Paire in Washington.

"It's very pleasing knowing that I can be mature and handle those situations very bravely, so I'm really happy with that," said Tsitsipas.

"I showed character out there. I played heroic tennis, I would say, in those crucial moments. That was very nice to see."

Paire – who fired down 12 aces and did not drop serve – defeated fifth seed John Isner 7-6 (7-3) 6-3 at the ATP 500 tournament.

Former US Open champion Cilic beat ninth seed Felix Auger-Aliassime 6-3 6-4 to reach the Washington quarters.

Auger-Aliassime's 11th double fault of the match allowed sixth seed Cilic to move through, with Medvedev waiting in the next round.

Medvedev – the third seed – saw off local favourite Frances Tiafoe 6-2 7-5.

Elsewhere, eighth seed Milos Raonic was stunned 6-4 6-4 by Peter Gojowczyk, Kyle Edmund rallied past Jo-Wilfried Tsonga 4-6 6-3 6-4, Norbert Gombos trumped Miomir Kecmanovic 1-6 6-3 7-6 (7-4) and Nick Kyrgios was a 6-2 7-5 victor against Yoshihito Nishioka.

Stefanos Tsitsipas and Nick Kyrgios moved into the Citi Open third round thanks to straight-sets wins on Wednesday.

Tsitsipas, the top seed, brushed past wildcard Tommy Paul 6-3 7-5 in their second-round clash in Washington.

The Greek star converted three of his eight break points to set up a last-16 meeting with Australian Jordan Thompson.

Thompson produced one of the upsets of the day, beating 14th seed Jan-Lennard Struff 6-7 (8-10) 6-4 7-5.

Kyrgios' run also continued, the Australian serving 24 aces in a 6-4 7-6 (7-5) victory over French 11th seed Gilles Simon.

Next up for Kyrgios is Yoshihito Nishioka, who edged seventh seed David Goffin 6-7 (5-7) 6-2 7-6 (7-5) after two hours, 40 minutes.

Of the 10 seeds in action, Simon, Goffin and Struff were three of five to make exits.

Pierre-Hugues Herbert was edged by Miomir Kecmanovic 3-6 6-4 7-6 (7-5) and Atlanta champion and last year's runner-up Alex de Minaur went down to lucky loser Peter Gojowczyk 6-3 7-6 (8-6).

Three-time runner-up John Isner cruised past Hubert Hurkacz 6-4 6-4, 2014 champion Milos Raonic beat Tim Smyczek 6-1 6-4 and Felix Auger-Aliassime edged Reilly Opelka 6-4 3-6 6-4.

Benoit Paire survived against Marc Polmans with a 6-3 6-7 (5-7) 7-6 (7-5) win and lucky loser Norbert Gombos overcame Adrian Mannarino 6-4 7-6 (11-9).

Meanwhile, in doubles action, brothers Andy and Jamie Murray got through their opener by beating Nicolas Mahut and Edouard Roger-Vasselin.

Frenchman Jo-Wilfried Tsonga celebrated his first victory at the ATP Citi Open after defeating Brayden Schnur en route to the second round.

Tsonga – the 2008 Australian Open runner-up – topped Canadian Schnur 6-4 7-6 (7-2) in Washington on Monday.

It meant Tsonga achieved a career first, having never won at the ATP 500 event in his 16-year career, with his only other Citi Open match resulting in defeat in 2009.

Tsonga, who improved to 22-12 for the year, will face second seed Karen Khachanov for a place in the third round.

Tommy Paul beat Denis Kudla 6-0 6-4 to set up a second-round clash with top seed Stefanos Tsitsipas, who was busy on Monday.

Tsitsipas and Australian star Nick Kyrgios teamed up on the doubles court for the first time, but they lost to top seeds Juan Sebastian Cabal and Robert Farah 6-3 3-6 10-5.

Elsewhere in the singles, 2016 finalist Ivo Karlovic was beaten by wildcard Bjorn Fratangelo 6-4 6-7 (14-16) 7-6 (7-5), Adrian Mannarino topped Ilya Ivashka 7-6 (7-3) 6-3 and Tim Smyczek was a 6-4 6-4 winner over Matthew Ebden.

Alexander Bublik claimed a 7-6 (7-5) 6-3 victory against Bradley Klahn, Malek Jaziri lost 6-2 6-4 to Marc Polmans, Hubert Hurkacz was too good for Donald Young 6-1 6-4, Lloyd Harris outlasted Ricardas Berankis 4-6 6-3 6-1, while Marius Copil triumphed 6-1 5-7 6-3 over Mikael Torpegaard.

At the Los Cabos Open, Thanasi Kokkinakis secured his first tour-level win since the 2018 Miami Open in March with a 6-4 6-4 victory against Maxime Janvier.

Marcel Granollers, Ernests Gulbis, Mikhail Kukushkin and Prajnesh Gunneswaran also advanced at the ATP 250 event in Los Cabos, Mexico.

Novak Djokovic cruised into the second round of Wimbledon with a straight-sets defeat of Philipp Kohlschreiber, but Alexander Zverev and Stefanos Tsitsipas fell at the first hurdle on day one.

Djokovic started the defence of his title with a 6-3 7-5 6-3 victory over German Kohlschreiber on Centre Court.

Sixth seed Zverev suffered more major misery as qualifier Jiri Vesely came from a set down to win 4-6 6-3 6-2 7-5 at the All England Club on Monday.

Thomas Fabbiano claimed the scalp of Austrlian Open semi-finalist Tsitsipas, the 89-ranked Italian triumphing 6-4 3-6 6-4 6-7 (8-10) 6-3.

Kevin Anderson, runner-up last year, got past Pierre-Hugues Herbert in straight sets, while the promising Felix Auger-Aliassime won got his first grand slam match win in an all-Canadian battle with Vasek Pospisil.

Ivo Karlovic, the oldest man to play in the singles since Ken Rosewall in1975 at the age of 40, saw off Andrea Arnaboldi to move into round two at SW19, but 16th seed Gael Monfils bowed out due to injury when trailing fellow Frenchman Ugo Humbert in the final set.

 

DJOKOVIC OVERCOMES NERVES TO SAIL THROUGH

World number one Djokovic said he was feeling the nerves, but it was not evident as he outclassed Kohlschreiber.

The top seed struck 37 winners and won 84 per cent of points on his first serve to set up an encounter with Denis Kudla in the second round.

Djokovic said: "I'm a human being, like anybody else. I do feel nerves. At the same time, I had a great, quality tennis player across the net who is very dangerous.

"I lost to him earlier in year [at Indian Wells]. The first match on grass, you slip a few times, still kind of finding the right position on the court, the right place. But I'm overall satisfied."

 

TSITSIPAS: I DESERVED STRAIGHT-SETS LOSS

Seventh seed Tsitsipas offered a brutally honest verdict after Fabbiano sent him crashing out.

"He was just better than me today. I think the way I played, it should have been in three [sets], not five," said the 20-year-old Greek.

"I don't know how I got to five. I guess with my fighting spirit, somehow I managed to win those two sets. He was just much more solid than me."

 

ZVEREV SUFFERING LACK OF CONFIDENCE

There was also a frank assessment from Zverev after he was beaten in the opening round of the grass-court major for the first time.

"One or two things don't go my way, and everything kind of a little bit falls apart," the world number five said. "It was kind of a typical grand slam match for me.

"I'm not very high on confidence right now. When I get to the important moments, I had, what, five, six break points in the fourth set alone? Can't take any of those.

"I had a 0-40, a 15-40. I'm down one break point myself and he takes it immediately, where I miss an easy volley. I didn't lose this match on tennis. It's just my confidence is below zero right now."

Wimbledon's opening day threw up some shocks in the men's draw after seeds Alexander Zverev and Stefanos Tsitsipas both made early exits.

Sixth seed Zverev lost his opening-round match to Czech world number 124 Jiri Vesely 4-6 6-3 6-2 7-5 on Court One.

Vesely has reached the last 16 at the All England Club in 2016 and 2018 and he will meet Pablo Cuevas in the second round.

"It was a great match, fantastic from beginning to end," he said. "Overall I think I played an unbelievable match without many mistakes.

"I was playing really well, serving good and trying to go to the net. The pressure was a little bit on him, but he won the first set and then I started to play. I had nothing to lose anymore."

Tsitsipas, the seventh seed, soon followed after being edged out by Thomas Fabbiano in a five-set thriller.

The Italian failed to take advantage of two match points in the fourth set only for the Greek to take it on a tie-break, however two breaks of serve in the final set proved decisive as he wrapped up a 6-4 3-6 6-4 6-7 (8-10) 6-3 victory.

Big-serving Croatian Ivo Karlovic now awaits Fabbiano in the second round.

Stefanos Tsitsipas waxed lyrical over Felix Auger-Aliassime after the sensation knocked him out of the Queen's Club Championships, describing the teenager as the most difficult opponent he has faced.

Auger-Aliassime made further waves ahead of Wimbledon by becoming the youngest man to reach the semi-finals at Queen's since Lleyton Hewitt in 1999 with a 7-5 6-2 defeat of Tsitsipas on Friday. 

Canadian Auger-Aliassime was a beaten finalist in his first tour-level grass-court tournament in Stuttgart last week and made another statement by claiming the scalp of top seed Tsitsipas in London.

The 18-year-old also beat Tsitsipas at Indian Wells this season and the world number six believes the rising star may be too good for Novak Djokovic, Rafael Nadal and Roger Federer.

Tsitsipas - who has already beaten Djokovic, Nadal and Federer - said: "He's the most difficult opponent I've ever faced, and I think it's gonna take a couple of tries to beat him.

"He's beaten me every single time we have faced each other: juniors and pro, he's beaten me at Indian Wells, he's beaten me here, he's beaten me a couple of times in juniors.

"I only beat him in doubles. I don't even count that one, because doubles is doubles. He has the whole package to play big, to beat – I'm sure if he ever gets the difficult chance to play Nadal, Djokovic or Federer – he's going to beat them, for sure.

"I will not be surprised if he gets wins over those guys. We will definitely see him in the top five. Maybe not this year but next year or the year after. I would expect something like this."

Auger-Aliassime will now face Feliciano Lopez in a battle between youth and experience after the Spaniard defeated sixth seed Milos Raonic 4-6 6-4 7-6 (7-5).

Gilles Simon came through a long all-French encounter with Nicolas Mahut 7-6 (7-5) 5-7 7-6 (7-3) and will come up against fourth seed Daniil Medvedev, a 6-2 6-2 winner over Diego Schwartzman.

Felix Auger-Aliassime sealed a second win of the day at the expense of Nick Kyrgios to reach the quarter-finals of the Queen's Club Championships and Diego Schwartzman knocked out defending champion Marin Cilic.

Kyrgios exchanged words with a chair umpire and peered over the fence at another match during a changeover before completing a 7-6 (7-4) 6-3 first-round victory over Roberto Carballes Baena on Thursday.

The Australian also reportedly berated himself for staying up until 3am playing a computer game on an eventful day in which he eventually bowed out with a 6-7 (4-7) 7-6 (7-3) 7-5 loss to Auger-Aliassime.

Auger-Aliassime and Kyrgios put on a show for a crowd that was relieved the weather held after two frustrating rainy days in London, the teenager having ousted Grigor Dimitrov 6-4 6-4 in the opening round.

Top seed Stefanos Tsitsipas will face Auger-Aliassime after completing a 6-3 7-5 win over Kyle Edmund prior to getting past Jeremy Chardy 4-6 7-6 (7-0) 7-6 (7-4).

Schwartzman sealed only his third win on grass, toppling Cilic 6-4 6-4, and will come up against Daniil Medvedev following the fourth seed's 7-6 (11-9) 6-7 (5-7) 6-4 defeat of Lucas Pouille.

Nicolas Mahut upset Stan Wawrinka 3-6 7-5 7-6 (7-2) and the qualifier's reward will be an all-French encounter with Kevin Anderson's conqueror Gilles Simon, while Milos Raonic ousted Aljaz Bedene to set up a showdown with Feliciano Lopez.

Lopez should not be short of support after linking up with Andy Murray to claim a doubles win over top seeds Juan Sebastian Cabal and Robert Farah in the Brit's latest return from hip surgery.

Andy Murray will face the Fever-Tree Championships' top seeds on his doubles return after the former world number one and Feliciano Lopez were drawn against Juan Sebastian Cabal and Robert Farah.

The event confirmed last week that two-time Wimbledon singles champion Murray would make his competitive comeback in the tournament having been out since January following a resurfacing operation on a longstanding hip problem.

The 32-year-old has not played since a five-set Australian Open loss to Roberto Bautista Agut and he and his Spanish partner Lopez have been handed a tough assignment against Colombian duo Cabal and Farah at Queen's.

In the singles draw, top seed Stefanos Tsitsipas will face Kyle Edmund first up while South African Kevin Anderson, another player making his comeback having been out since March with an elbow injury, will meet Cameron Norrie.

Dustin Brown pulled off a huge upset by beating fellow German Alexander Zverev at the Stuttgart Open and Stefanos Tsitsipas also made a losing start to the grass-court season.

Brown had not won a main-draw match on the ATP Tour since the 2017 US Open before this week, but the enigmatic showman is through to the quarter-finals in his homeland after a stunning 6-4 6-7 (3-7) 6-3 defeat of the top seed.

Zverev, playing his first match since a French Open quarter-final defeat to Novak Djokovic, paid the price for converting only one of 14 break points and double-faulted 14 times in a stunning loss.

The 170-ranked Brown showed great athleticism at the age of 34, breaking the world number five on three occasions in a typically entertaining performance on Thursday.

Qualifier Brown will now face Felix Auger-Aliassime, a 7-5 6-4 winner in the final match of the day against Gilles Simon.

The top five seeds have all made early exits in Germany, with Karen Khachanov losing 6-4 6-2 to Matteo Berrettini and Denis Kudla beating Gael Monfils after Daniil Medvedev and Nikoloz Basilashvili crashed out on Wednesday.

Tsitsipas bowed out of the Rosmalen Grass Court Championships as Nicolas Jarry defeated the top seed 6-4 3-6 6-4.

Jarry served 13 aces and broke twice to claim the scalp of the 20-year world number six in 's-Hertogenbosch.

Fernando Verdasco was another seed who was second best, Adrian Mannarino rallying from a set down to win 1-6 6-3 6-4 and advance along with David Goffin and Cristian Garin.

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