Hubert Hurkacz will contest the second ATP 1000 final of his career after coming from a set behind to defeat world number five Casper Ruud 5-7 6-3 6-2 in the semi-final of the Canadian Open on Saturday.

It was an interesting clash of styles going into the contest, with Hurkacz expected to rely on his dominant serve, while Ruud is one of the game's top returners, so when Ruud responded to an early break and was the one serving up a storm, it spelled trouble for the world number 10.

Ruud landed 78 per cent of his first serves in the opening set, compared to 60 per cent for Hurkacz, and the Norwegian won 95 per cent of those points (20-of-21) to allow just one break point in the frame while creating four for himself.

As Ruud's serve began to falter – with his first serve accuracy and effectiveness both cratering in the second and third set – his game began to struggle to hold up to the metronomic consistency of Hurkacz, who won the ace count 18-to-eight.

After pulling the match even at one set each, Hurkacz took the contest by the scruff of the neck and won the first four games of the deciding frame to pull away.

Poland's Hurkacz – who won his only previous ATP 1000 final against Jannik Sinner at the 2021 Miami Open – will now face Pablo Carreno-Busta in the decider after the Spaniard prevailed in a three-hour war of attrition against Daniel Evans 7-5 6-7 (7-9) 6-2.

In a match that was close in every area, Carreno-Busta was slightly better, winning 68 per cent (68-of-100) of his service points compared to 60 per cent (66-of-110) for Evans, while committing just one double fault compared to the Englishman's six.

It will be Carreno-Busta's first ATP 1000 final appearance, with the 2021 Hamburg Open – an ATP 500 event – the only career title for the 31-year-old above the ATP 250 level.

Nick Kyrgios' red-hot form has been halted after going down in three sets to eighth seed Hubert Hurkacz in the quarter-finals of the Canadian Open on Friday.

Hurkacz ran away with victory, triumphing 7-6 (7-4) 6-7 (5-7) 6-1 in one hour and 46 minutes in Montreal.

Wimbledon finalist Kyrgios had come into the encounter fresh from winning 15 of his past 16 matches, including lifting the title at last week's Washington Open. Kyrgios' run had fueled expectations around him at the upcoming US Open.

"Nick has been playing some incredible tennis throughout the past weeks, so it is a pleasure playing against him," Hurkacz said post-match in his on-court interview.

"I started really well. Nick was maybe a little bit injured, which might have hurt his serve. With both of us serving so well, that few per cent can make the difference."

Kyrgios was quick on serve but the 25-year-old Pole eventually ground him down, prevailing in the third set aided by an early break.

That break came after Kyrgios gave up two double faults, leading to the Australian to complain to the umpire about his opponent's mid-match break for a change of clothes.

The Australian was unable to break Hurkacz's serve throughout the match, with the Pole edging the aces count 20-19, while he was also superior on return. Kyrgios had more winners (55-47), but more unforced errors (24-13).

Hurkacz, who will face fourth seed Casper Ruud in the semi-finals, is the only former Masters 1000 champion left in the draw.

Ruud cruised into the last four with a 6-1 6-2 victory over hometown hero Felix Auger-Aliassime who was brushed aside in one hour and 14 minutes.

The Norwegian's win marks his third ATP Masters 1000 semi-final of the season, with the Canadian plagued by 21 unforced errors compared to Ruud's eight.

Unseeded Briton Daniel Evans fought back from a lopsided opening set to knock off Tommy Paul 1-6 6-3 6-4.

Evans will face Spaniard Pablo Carreno Busta after he defeated Jack Draper 7-6 (7-4) 6-1 in just under two hours.

Australia's Nick Kyrgios has now won 15 of his past 16 matches after defeating compatriot Alex de Minaur 6-2 6-3 in the third round of the Canadian Open – with his only loss coming in the Wimbledon final against Novak Djokovic.

Fresh off his first singles title since 2019 when he won last week's Washington Open, Kyrgios collected his ninth consecutive victory in impressive fashion, showing no difficulty in navigating his first-ever matchup against his fellow countryman.

He won the first four games of the match, and snatched a break in the first game of the second set to book his quarter-final against Poland's Hubert Hurkacz.

Hurkacz, the eighth seed, had to come back from a set down to defeat Spain's Albert Ramos-Vinolas 6-7 (6-8) 6-2 7-6 (7-3). He struggled with his serve early, with four double faults in the opening frame, but cleaned it up as the match went on, double-faulting only once in the last two sets.

England's top hope Cameron Norrie suffered a disappointing 6-3 6-4 defeat at the hands of world number nine Felix Auger-Aliassime, but Daniel Evans and Jack Draper made it through to fly the flag.

Evans pulled off an upset win to beat 10th seed Taylor Fritz 7-6 (7-5) 1-6 7-5, and 20-year-old Draper was up a set when 17th seed Gael Monfils retired with an injury at 6-2 0-2.

American Tommy Paul claimed another scalp with his 6-4 6-2 victory against 13th seed Marin Cilic, giving him back-to-back wins against top-15 opponents after emerging triumphant against Carlos Alcaraz in the previous round.

In the final match of the day, Pablo Carreno-Busta beat his third top-30 opponent of the week with a 6-2 6-4 result against Italy's Jannik Sinner, following strong successes against Matteo Berrettini and Holger Rune.

Second seed Hubert Hurkacz was a shock second-round casualty from the Citi Open on Wednesday after a straight-sets defeat to Emil Ruusuvuori.

World number 46 Ruusuvuori triumphed 6-4 7-6 (7-3) in one hour and 43 minutes to book a quarter-final spot.

Hurkacz, who is ranked 11th in the world and reached last year's Wimbledon semi-finals, fought hard but failed to capitalise on four break points throughout the match.

"He had an early break point, but then I was able to keep that service game and give myself a chance to break him and I was able to use it and then just try to keep my own serve," Ruusuvuori said.

"I just tried to hang in there and tried to stay as tough as [I] can."

Wimbledon runner-up Nick Kyrgios defeated 14th seed Tommy Paul 6-3 6-4 in one hour and 25 minutes.

The Australian hit 29-21 winners, with the majority coming from his serve and forehand, sending down 15 aces, winning 84 per cent on his first serve.

Kyrgios, who broke Paul in his opening service game, converted three of four break points for the match, while the American failed to capitalise on any of his four.

Sixth seed Denis Shapovalov was bundled out in the second round by American wildcard J.J. Wolf 6-2 6-7 (5-7) 6-3 in a major upset.

Third seed Taylor Fritz avoided an early exit with a 6-4 6-4 win over Australian Alexei Popyrin in one hour and 11 minutes, while fourth seed Reilly Opelka came from a set down to defeat Denis Kudla 6-7 (6-8) 6-4 6-4 in just over two hours. Opelka sent down 28 aces across the match.

Fifth seed Grigor Dimitrov got past Adrian Mannarino 6-1 3-6 7-5 and ninth seed Holger Rune brushed off Benoit Paire 6-3 6-2.

Francis Tiafoe defeated Christopher Eubanks 6-3 7-6 (7-2), while 13th seed Maxime Cressy fought back from an early deficit to get past Jack Sock 4-6 6-4 6-0 to set up a third-round clash with top seed Andrey Rublev.

There were defeats for 11th seed Alex de Minaur to Yoshihito Nishioka 3-6 7-6 (8-6) 6-2, 12th seed Sebastian Baez against Sebastian Korda 6-1 6-4 and 15th seed Aslan Karatsev against Andy Murray's first-round conqueror Mikael Ymer 6-4 3-6 6-4.

At the Los Cabos Open in Mexico, second seed Felix Auger-Aliassime had no troubles against local Juan Alejandro Hernandez Serrano, winning 6-3 7-5.

American sixth seed Brandon Nakashima also progressed into the quarter-finals with a 6-3 6-3 win over Max Purcell, while Miomir Kecmanovic beat Jordan Thompson 6-4 6-2.

Hubert Hurkacz sent down 21 aces in his first-round match at Wimbledon, enough to raise €2,100 for the people of Ukraine but not enough to reach the second round.

The seventh seed, who was a semi-finalist at the All England Club last year, promised on the eve of the championships to donate €100 in aid for every one of his aces.

"Hope my serve works well," Hurkacz wrote on Twitter, and it certainly did across five sets against Alejandro Davidovich Fokina.

Having averaged 11.6 aces per match this season – his 452 the third most on the ATP Tour – Hurkacz had 21 to just three double faults in an effective serving display on Monday.

Unfortunately, Davidovich Fokina was still able to pull off an early upset, narrowly advancing 7-6 (7-4) 6-4 5-7 2-6 7-6 (10-8).

This was the third top-10 win of Davidovich Fokina's career but the first on grass, with his previous two such victories both coming at the Monte-Carlo Masters (vs Matteo Berrettini in 2021 and versus Novak Djokovic in 2022).

While Hurkacz will not add to his ace tally, John Isner undoubtedly will.

He had a remarkable 54 in his five-set win against Enzo Couacaud – as many as Hurkacz managed across six matches in his 2021 run to the last four.

The last player to record 50 or more aces in a grand slam match had also been Isner, against Steven Johnson at the 2020 US Open.

Hubert Hurkacz revelled in defeating the "the best player in the world" after downing Daniil Medvedev in straight sets to lift the Halle Open title.

Medvedev replaced Novak Djokovic as the world number one last Monday, just a day after the Russian fell to a surprise final defeat against Tim van Rijthoven at the Rosmalen Grass Court Championships.

The 26-year-old followed that up with another final appearance in Halle, where he was convincingly beaten 6-1 6-4 by world number 12 Hurkacz.

That made Hurkacz the seventh male player in the Open Era to win his first five career finals, while Medvedev has lost all three showpieces he has contested in 2022.

The US Open success in September was the last trophy Medvedev lifted, but Hurkacz lavished praise on his opponent after the match on Sunday.

"Daniil is an unbelievable player," said Hurkacz. "He's the best player in the world, so it's very tricky to play him.

"All the right shots went my way at the beginning, so I definitely gained a lot of momentum from that. 

"I'm super excited. I've been waiting a little for my first [title] this year. I'm happy to win my first ATP 500 title and of course, on the grass it is very special.

"I was serving pretty good today and got a bit of momentum from the first game.

"I saved a couple of deuces on my service game, and then I managed to break Daniil’s serve so I definitely got a bit of momentum. I'm very happy with the win in front of such a great crowd here."

Medvedev boasted a 14-2 record on grass since a first-round exit at Halle last year before meeting Hurkacz, who came in for praise from the world number one.

"Congrats Hubert, great match today, great week. Congrats to you and your team," he said at the post-match ceremony.

"You guys are super nice. Hopefully a lot more matches to play on the biggest stage. Congrats for a great week and the title."

Medvedev was frustrated throughout the match, repeatedly shouting at coach Gilles Cervara, who stormed out of his seat early in the second set.

While he did not address the topic after the final, Medvedev apologised to the crowd for "not making this match longer and more interesting" and acknowledged he was "not easy to be with on the court" this week.

Daniil Medvedev lost a second final in two weeks as he fell to a straight-sets defeat to Hubert Hurkacz at the Halle Open on Sunday.

The world number one struggled to get going and repeatedly took his anger out on coach Gilles Cervara, who stormed out of his seat early in the second set.

Top seed Medvedev had already lost the first set 6-1 by that point and only fared slightly better in the second, which ended 6-4 in Hurkacz's favour.

Hurkacz has now won five ATP Tour titles, with this his first on grass, while Medvedev remains stuck on 13 having lost all three finals he has competed in this season.

The most recent of those losses came at the hands of world number 106 Tim van Rijthoven last week, but Medvedev had not dropped a set en route to Sunday's clash in Halle.

Indeed, Medvedev was 14-2 on grass since a first-round exit at Halle last year, yet Hurkacz broke the Russian's first two service games and eased into a 5-0 lead.

Having successfully served out the opener, Hurkacz – who beat the same opponent in this year's Miami Masters – again broke Medvedev in the first game of the second set.

Medvedev took aim at his coach at that point, with Cervara then spotted leaving the stands and failing to return for the remaining nine games, which went the way of the serve.

After easily navigating his way past Medvedev in a match lasting just over an hour, fifth seed Hurkacz becomes the seventh male player in the Open Era to win his first five career finals.

Daniil Medvedev set up a Halle Open final meeting with Hubert Hurkacz, overcoming home favourite Oscar Otte to reach his second grass-court final in as many weeks.

The world number one was forced to save a set point in a tight opener before rallying in a tie-break and sailing through the second set in a 7-6 (7-3) 6-3 win. 

Despite falling to a shock defeat to Tim van Rijthoven in 's-Hertogenbosch last week, Medvedev is now 14-2 on grass since a first-round exit at Halle last year, and was delighted to make up for 2021's performance on one of his favoured surfaces. 

"I didn't play well in Halle last year, so I'm happy that this year I managed to raise my level," he said after the win.

"As I've always said, I love playing on grass, so I'm happy to show to myself that I'm capable of being in the final of one of the greatest tournaments, especially on grass, and of course I'm looking forward to tomorrow."

Standing between Medvedev and the second grass-court title of his career is Hurkacz, who required two tie-breaks to edge a thrilling contest with Nick Kyrgios, winning 4-6 7-6 (7-2) 7-6 (7-4).

Elsewhere, last year's Wimbledon runner-up Matteo Berrettini remains on course for back-to-back titles at the Queen's Club Championships after a straight-sets win over Botic van de Zandschulp in the final four.

Berrettini overcame a rain stoppage to secure his eighth consecutive victory, securing a 6-4 6-3 win, and delighted after triumphing in challenging conditions.

"It was a really tough match. We stopped for the rain. I had a lot of chances. It was windy again and really tough to play, but I definitely think it was the best match of the week, so I am really happy and looking forward to the final," the Italian said. 

Berrettini will face world number 48 Filip Krajinovic in Sunday's final, after the Serb cruised past 2014 US Open champion Marin Cilic 6-3 6-3.

Daniil Medvedev ended his wait for a first win over Roberto Bautista Agut at the Halle Open as his impressive start to the grass-court season continued.

The world number one, who reached the final at 's-Hertogenbosch last week only to suffer a shock defeat to Tim van Rijthoven, had not beaten Bautista Agut in three previous matches.

But his duck against the Spaniard is over following a 6-2 6-4 win, which set up a semi-final meeting with Oscar Otte after the German saw off Karen Khachanov in three sets.

"I remember all the matches we had… He was playing some [great] tennis and it was tough for me to win," Medvedev said of his previous meetings with Bautista Agut. 

"Today I had my plan, managed to keep it going. Definitely got more edge on the most important points, because he had more break points than me. It was not easy, and I'm happy to win."

Hubert Hurkacz, a Wimbledon semi-finalist last year, is also into the last four after edging Felix Auger-Aliassime in two tie-breaks and will face Nick Kyrgios, who beat Paulo Carreno Busta in straight sets.

Elsewhere, Matteo Berrettini was victorious at the Stuttgart Open and is on course to go back-to-back at the Queen's Club Championships after seeing off Tommy Paul 6-4 6-2 to progress to the semi-finals.

Botic van de Zandschlup is his next opponent, the Dutchman overcoming Alejandro Davidovich Fokina 6-2 6-4.

Meanwhile, Filip Krajinovic had to come from a set down to end Briton Ryan Peniston's run at the quarter-final stage, with his reward a meeting with former US Open champion Marin Cilic, a straight-sets victor over Emil Ruusuvori.

A spirited fightback from Nick Kyrgios saw the Australian beat second seed Stefanos Tsitsipas in the Halle Open on Wednesday.

Kyrgios suffered a disappointing semi-final defeat to Andy Murray in Stuttgart last week, but looked greatly improved against Tsitsipas as he recovered from a set down to win 5-7 6-2 6-4.

It was the second serve of both men where Kyrgios shone, winning 76 per cent (28 of 37) of points on his second serve, and 58 per cent (23 of 40) on his opponent's.

"Stef is one of the best players in the world at the moment and he's going to have some amazing results and I'm sure many, many grand slams," Kyrgios said following his win.

"I don't know if I can say the same for me, but I'm happy to still be able to produce this level with the tournaments I play. It is a testament to how hard I do work when I'm not playing."

He will face Pablo Carreno Busta in the quarter-finals after the Spanish sixth seed beat Sebastian Korda 6-4 0-6 6-3.

Elsewhere, Hubert Hurkacz will face Felix Auger-Aliassime in the last eight after defeating Ugo Humbert 7-6 (7-5) 6-3, while the Canadian also won in straight sets against Mackenzie McDonald 7-6 (9-7) 6-1.

The one remaining first round match saw number one seed Daniil Medvedev beat David Goffin 6-3 6-2 to set up a second round clash with Ilya Ivashka.

At the Queen's Club Championships, sixth seed Denis Shapovalov was eliminated by Tommy Paul 6-4 2-6 6-4, with the American now scheduled to face Stanislas Wawrinka in the second round.

It means that six of the eight seeds in west London were knocked out in the first round, with Matteo Berrettini and Marin Cilic the only remaining seeds. The latter sealed his place in the quarter-finals on Wednesday with a 7-6 (8-6) 7-5 win over Alexander Bublik.

Cilic will play Finland's Emil Ruusuvuori in the last eight after he beat home favourite Jack Draper 6-2 7-6 (7-2).

The best contest of the day came between Alejandro Davidovich Fokina and Alex de Minaur, with the former coming from behind to win 4-6 6-4 7-5 to set up a quarter-final with Botic van de Zandschulp, who beat Grigor Dimitrov 7-6 (7-5) 6-3.

Top seed Casper Ruud suffered a shock first-round exit at the Queen's Club Championships, going down in straight sets to British ATP Tour debutant Ryan Peniston in west London.

The French Open runner-up struggled to get going as he fell to a 7-6 (7-4) 7-6 (7-2) defeat to the world number 180, who was backed by a boisterous home crowd throughout.

Ruud struggled from the off as Peniston forced four break points in the Norwegian's first service game, and his miserable outing was rounded off when his opponent raced into a 5-1 lead before serving out a second-set tie-break.

After claiming the scalp of the world number five, Peniston told the BBC: "I can't really believe it. It feels like a dream. It doesn't feel real.

"I think I've been playing well. Casper is an unreal player and he did so well at the French Open, so I knew it was a tough ask. Four or five years ago I was sitting in the crowd just watching so to be here now is just unreal."

Ruud was not the only big name to fall at the first hurdle, with fifth seed Diego Schwartzman going down 6-1 6-4 against big-serving Sam Querrey to become the fourth of the top five seeds to fail to reach the round of 16.

Second seed and defending champion Matteo Berrettini is the exception after faring much better against another home favourite, cruising past Dan Evans 6-3 6-3, while Stan Wawrinka downed Francis Tiafoe 7-6 (7-2) 6-7 (6-8) 7-6 (7-5), and Denis Shapovalov's clash with Tommy Paul was suspended by darkness at one set apiece. 

Elsewhere, world number six Stefanos Tsitsipas progressed through his opening match at the Halle Open, beating Benjamin Bonzi 7-6 (7-1) 1-6 6-3 to set up an enticing last-16 clash with Nick Kyrgios, who bested Daniel Altmaier 6-3 7-5.

Fourth seed Felix Auger-Aliassime also progressed after being taken to three sets, beating Marcos Giron 6-3 5-7 6-3.

Meanwhile, defending champion Ugo Humbert will face a tough round-of-16 match against fifth seed Hubert Hurkacz after the Pole overcame Maxime Cressy 6-4 4-6 6-4. 

Daniil Medvedev started his grass-court season with victory over Gilles Simon in the Rosmalen Grass Court Championships, while Hubert Hurkacz and Denis Shapovalov suffered shock defeats in Stuttgart.

Medvedev will replace Novak Djokovic at the top of the rankings next Monday and the Russian could celebrate by claiming a first title of the year in ‘s-Hertogenbosch.

The top seed, who will not compete at Wimbledon due to a ban on Russian and Belarusian players, beat Frenchman Simon 7-5 6-4 on Thursday after saving three set points and storming back from 5-2 down in the opener, setting up a quarter-final against lya Ivashka.

Felix Auger-Aliassime, the second seed, defeated Tallon Griekspoor 7-6 (7-2) 7-6 (7-5), but third seed Taylor Fritz was beaten by wildcard Tim van Rijthoven in straight sets.

Alex de Minaur and Jenson Brooksby also made early exits, losing to French duo Adrian Mannarino and Hugo Gaston respectively.

Marton Fucsovics claimed the scalp of third seed Hurkacz to reach the last 16 at the Stuttgart Open, winning 7-5 6-7 (7-) 6-3

Shapovalov also lost his opening of the grass-court season, Oscar Otte getting the better of the fourth seed 7-6 (8-6) 7-6 (7-4)

There was no such trouble for top seed Stefanos Tsitsipas, who beat Dominic Stricker 6-3 6-4, and Andy Murray accounted for seventh seed Alexander Bublik in straight sets.

Casper Ruud described his French Open win over Hubert Hurkacz as the "perfect" way to tee up his first grand slam quarter-final appearance, as the eighth seed looks to extend the best major run of his career. 

Ruud downed Hurkacz 6-2 6-3 3-6 6-3 in 2 hours and 31 minutes on Monday to make the last-eight of the singles draw at a grand slam for the first time in his career, bettering his run to the fourth round at the Australian Open last year.

The Norwegian will face talented teenager Holger Rune for a spot in the semi-finals after the 19-year-old became the first Danish man to reach a grand slam quarter-final in the Open era by eliminating Stefanos Tsitsipas.

Speaking at his post-match news conference, Ruud said the win featured some of his best tennis this year.

"I feel good, of course. It's a good result. To make my first quarter-final here in Roland Garros means a lot. It's the first grand slam that I visited as a kid," he said.

"It's nice to get one of my best results of my career so far here. I hope I can continue the level of my tennis and [keep] the streak going.

"Today I think I played some of my best tennis this year for the first two sets. [In the] fourth set as well, I played well when I had to come back.

"I think that's a perfect way to go into a quarter-final for me. Hopefully I can reach a step or two or three more."

After recording his career-best major performance, Ruud – who lost his first ATP 1000 final to Carlos Alcaraz at the Miami Open in April – was keen to go further, saying he will only allow himself to look back upon the milestone at the end of his campaign.

"Well, I mean, of course, it's a new milestone. [But] when I'm playing the tournament, playing the match, I don't really think too much about it," he added.

"Of course, when I'm done with this or when this tournament is over for me, I will look back and think that I did a good job and did a good result and made my best result in a grand slam.

"It is going to change, of course, the way I think I look at the grand slams in the future, when you know you have reached a quarter-final one time. It has been a big goal for me this year, and to reach it is a good feeling.

"But of course, when you reach a goal, you make new goals. That's usually how it goes. My new goal will be in a few days' time to try to reach the semi-final."

With many of the game's biggest names, including Novak Djokovic, Rafael Nadal and Carlos Alcaraz all landing on the opposite side of the draw to Ruud, the 23-year-old may not get too many better chances to enjoy a deep grand slam run.

And the Norwegian suggested pundits may have placed too much focus on a few big names in the build-up to Roland Garros, adding: "Before the tournament, there was, of course, already a lot of talk who the favourite was.

"I think everyone was talking about the top half of the draw with Nadal, Djokovic and Alcaraz of course there, [but] there are many other good players in the tournament." 

Reigning Monte Carlo Masters champion Stefanos Tsitsipas will have to overcome Alexander Zverev if he is to have the chance to defend his title.

Zverev, who is ranked third in the world - two places higher than Tsitsipas - fought back to defeat Jannik Sinner 5-7 6-3 7-6 (7-5) in his quarter-final match, denying his opponent another top-five seed scalp following his prior win over Andrey Rublev.

"It means a lot, definitely, especially [with] how this year has been going so far for me," said Zverev after a gruelling three hours on court.

"I've lost long matches like that, so I’m happy I won this one."

Tsitsipas also orchestrated a superb turnaround against Diego Schwartzman, prevailing 6-2 6-7 (3-7) 6-4.

The Greek had looked set for a last-eight exit at four games down in the final set, only to stage a dramatic comeback to keep his hopes of a first title since last May's Lyon Open alive.

"There was a moment in the match where I felt what I was doing wasn't working," Tsitsipas said.

"He had a massive lead and momentum in what he was trying to do. I just tried to stay in the match as much as I could and that worked out very well.

"I wasn't expecting much at that point being a double break down, so I relaxed at that point."

Schwartzman meanwhile will rue his inability to put the tie to bed, having already reached two ATP finals this year.

Grigor Dimitrov and Alejandro Davidovich Fokina will face off in the other semi-final.

Bulgarian Dimitrov beat off Hubert Hurkacz in another final-set tie-break, winning 6-4 3-6 7-6 (7-2).

Fokina, who eliminated Novak Djokovic in the second round, turned over Indian Wells champion Taylor Fritz in another comeback result, triumphing 2-6 6-4 6-3.

Alexander Zverev and Stefanos Tsitsipas progressed to the quarter-finals of the Monte Carlo Masters with straight sets wins on Thursday, remaining on course for a final meeting.

Last year's runner-up Andrey Rublev, however, missed out on a last-eight spot after falling to a three-set defeat against Jannik Sinner.

World number three Zverev overcame Spain's Pablo Carreno Busta 6-2 7-5 to progress in Monaco, where he is seeking to win the sixth ATP 1000 title of his career.

"For the second clay-court match of the season, I can't complain too much," the 24-year-old second seed said on court after sealing the victory.

"Yes, I lost focus a little bit in the second set, but at the end of the day, he's somebody that can really play. I'm happy with a two-set win."

Tsitsipas (3) remains in contention for a second consecutive title in the principality after defeating Laslo Dere 7-5 7-6 (7-1) and will face off against 12th seed Diego Schwartzman for a semi-final spot after the Argentine defeated Lorenzo Musetti in a hard-fought three-set encounter.

There will be no repeat of 2021's final between Tsitsipas and Rublev, however, after the Russian fell to a thrilling 5-7 6-1 6-3 loss to ninth seed Sinner in the day's final contest.

The other seed to fall victim to a shock in the last 16 was world number seven Casper Ruud, losing 6-3 7-5 to Grigor Dimitrov, who will face Poland's Hubert Hurkacz in the last eight. 

Finally, Novak Djokovic's conqueror Alejandro Davidovich Fokina cruised past David Goffin 6-4 6-1 to set up a quarter-final tie with the United States' Taylor Fritz, who bested compatriot Sebastian Korda – with whom he played doubles with in Monte Carlo – in straight sets.