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.

Daniil Medvedev showed on Thursday why he is the top overall seed at the Los Cabos Open, comfortably handling the challenge of Ricardas Berankis in a 6-2 6-2 win.

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.

Nick Kyrgios barely broke a sweat on his way to a 6-3 6-2 win against Marcos Giron in the opening round of the Washington Open, finishing the job in an even 60 minutes.

The talented Australian, who won the doubles title at last week's Atlanta Open with compatriot Thanasi Kokkinakis, showed off his imposing serve against Giron. He won the ace count 12-to-four, while converting 82 per cent (28-of-34) of his successful first serves into points.

Earlier in the day, Daniel Evans won an all-English showdown against Kyle Edmund 6-1 6-2, but fellow Englishman Jack Draper was not so lucky against Russia's Andrey Rublev, going down 6-4 6-2.

Winner of the singles title at the Atlanta Open, Jenson Brooksby could not keep his strong form going as he lost 6-4 6-3 to Yoshihito Nishioka. Mackenzie McDonald lost to Brooksby in Atlanta, and he was also bounced in the first round by Finland's Emil Ruusuvuori 1-6 6-4 6-4.

America's Chris Eubanks won a tough three-setter against France's Benjamin Bonzi 3-6 6-3 7-5, and Sebastian Korda passed the test of in-form Ilya Ivashka 6-4 7-6 (7-5).

Veteran Jack Sock got the better of Belgium's David Goffin 7-6 (7-4) 6-4, and the Netherlands' Botic van de Zandschulp fought off frisky Croatian Borna Gojo 7-6 (8-6) 6-7 (5-7) 6-4 to narrowly avoid an upset from a player ranked 170 spots lower.

Meanwhile, at the Los Cabos open in Mexico, Kokkinakis continued his march back up the rankings with a 6-3 6-7 (5-7) 6-2 win against Fernando Verdasco.

Kokkinakis will play American Steve Johnson in the second round after he collected a straight sets 7-6 (7-1) 6-4 win against Argentina's Gonzalo Villanueva.

Romania's Radu Albot defeated Spain's Feliciano Lopez 6-3 6-7 (6-8) 6-3 to book his place in the second round against Australian Jason Kubler, who won his 10th match from his past 12 fixtures to beat Tomas Martin Etcheverry 6-7 (4-7) 6-3 6-1.

The only Mexican in the draw, Alex Hernandez, made the most his wildcard to win his first tour-level match, defeating Nicolas Barrientos 3-6 6-4 6-4 to become the first Mexican player to win at Los Cabos.

Facundo Bagnis was the only of the three Argentines to make it through, with a 6-3 6-1 win over Ernesto Escobado, Brandon Nakashima defeated Kaichi Uchida 7-6 (7-1) 6-2, and Jordan Thompson rounded out the day's action with a comfortable 6-3 6-0 triumph over Yannick Hanfmann.

Ryan Peniston stunned French Open quarter-finalist Holger Rune at the Eastbourne International to continue his strong form on the grass.

Peniston beat world number five Casper Ruud as he reached the quarter-finals at the Queen's Club Championships last week, and followed that up by recovering from a set down against Rune to reach Eastbourne's last 16 in impressive fashion.

After wrapping up a 4-6 7-6 (7-5) 6-1 win, the 26-year-old told the home crowd: "I'm very happy with that. A tough start but I managed to fight, thanks to you guys.

"Since Queen's it has been madness. A couple of weeks ago was a lot different and things have changed, but I'm loving it."

Rune, who was twice two points from victory in an enthralling contest, was jeered by spectators after hitting a ball out of court and kicking his towel bin after being broken in the third set.

Peniston will face Pedro Martinez in the next round after he benefited from fellow Spaniard Alejandro Davidovich Fokina being forced to retire at one set apiece, while Ugo Humbert fell to a 6-7 (2-7) 6-3 6-4 reverse against Brazil's Thiago Monteiro.

Lorenzo Sonego posted a 4-6 7-6 (7-5) 7-6 (7-1) win over James Duckworth, while Tommy Paul recovered from a set down to beat Francisco Cerundolo and home favourite Dan Evans overcame Adrian Mannarino 6-4 6-3.

The seeds in action at the Mallorca Open endured mixed fortunes as Sebastian Baez cruised past Jordan Thompson in straight sets, but Botic van de Zandschulp was beaten by Marcos Giron.

The Dutchman succumbed to a 6-7 (6-8) 6-4 7-6 (7-2) defeat, while Germany's Daniel Altmaier beat Dusan Lajovic 7-5 7-6 (7-2).

Nick Kyrgios set up an enticing last-16 meeting with fifth seed Roberto Bautista Agut by knocking out Serbia's Laslo Djere in a marathon three-set contest, recovering to win 5-7 7-6 (7-1) 7-6 (7-1).

Stan Wawrinka said he was "feeling great" after securing his first win in 15 months by downing 14th seed Reilly Opelka at the Internazionali d'Italia.

The three-time grand slam winner made his tour return last month after requiring two surgeries on a left foot injury, but rallied after losing his first set against Opelka to secure a memorable 3-6 7-5 6-2 first-round victory.

Speaking after booking a second-round meeting with Laslo Djere, who beat Borna Coric 6-2 6-7 (3-7) 6-2, Wawrinka said his desire to play at the top level never left him, despite his injury woes.

"I think in general I was feeling good on the court, physically I was feeling great," he said. "For sure, when you don't win a match in more than a year, you start to think about it more than you should and not focus on the right things. 

"In general, I think it was a great match, a great battle. I stayed positive. I started to feel much better with my tennis by the end of the second set, and in the third set. I'm really happy with this victory.

"After two surgeries, at my age I could easily have stopped playing because my career is way better than what I expected when I was young.

"But I still have this fire in me. I still believe that I can play great tennis. I still believe that I make some big results, maybe not now, but in a few months."

Fellow former grand slam champion Dominic Thiem, who also returned from a long injury-enforced absence last month, fared less well, going down in straight sets to Fabio Fognini.

Having lost to Andy Murray at the Madrid Open last time out, 2020 US Open winner Thiem is still chasing his first victory of the year after losing 6-4 7-6 (7-5) to the 34-year-old Italian.

Elsewhere, 13th seed Denis Shapovalov edged an epic three-hour contest against Italy's Lorenzo Sonego 7-6 (7-5) 3-6 6-3, responding after being handed a game penalty for shouting expletives at a partisan crowd in Rome during the second set.

The frustrated Canadian was heard to tell spectators: "Shut the f*** up" when being booed after complaining about a second serve being called out by the umpire, but eventually regained his composure to claim a three-set win.

Shapovalov will face Georgia's world number 25 Nikoloz Basilashvili in the second round after he overcame Daniel Evans 7-6 (7-2) 6-2, while the only other seed to play on Monday, Spain's Pablo Carreno Busta, cruised to a 6-3 6-2 victory over Federico Delbonis.

There were victories for John Isner and Dan Evans as the Madrid Open got up and running on Sunday.

Big-serving American Isner overcame Filip Krajinovic 7-6 (10-8) 6-4 and will face either Cameron Norrie or Kwon Soon-woo in the round of 32.

Isner is joined in the next round by Evans, who eased past Federico Delbonis 6-3 6-4 to set up a last-32 meeting with either Roberto Bautista Agut or Jenson Brooksby.

Fellow Briton Jack Draper also enjoyed a straight-sets victory, edging out Lorenzo Sonego 6-4 6-3 to book a clash with number six seed Andrey Rublev, who received a bye.

Monday's action will see wildcard Andy Murray face Dominic Thiem and 10th seed Jannik Sinner take on Tommy Paul.

Jannik Sinner saved three match points to avoid a shock defeat to Alejandro Davidovich Fokina in the first round of the Dubai Tennis Championships.

After losing the first set, the world number 10 staved off defeat in a nerve-wracking second-set tie-break.

The fourth seed clung on as Davidovich Fokina saw a trio of opportunities to clinch a shock win go begging, the Spaniard made to pay as his Italian counterpart fought back to prevail 4-6 7-6 (8-6) 6-3.

Sinner, who will next face former world number one Andy Murray, said: "It was a very tough match. I know him, but we've never played against each other.

"It was the first time for both of us and it was a tricky one, saving three match points. On the first one I got lucky because it was out, but not so far [out]."

Second favourite Andrey Rublev won both the singles and doubles titles in Marseille last week and continued his fine form with a 6-4 7-5 win over Daniel Evans that saw the Russian send down 28 winners.

Sixth seed Denis Shapovalov had to recover from a set down to see off Marton Fucsovics, though fifth seed Hubert Hurkacz enjoyed a more routine straight-sets triumph over Alexander Bublik.

Eighth seed Roberto Bautista Agut made relatively light work of Arthur Rinderknech but defending champion and seventh seed Aslan Karatsev was stunned 7-5 6-3 by Mackenzie McDonald.

Karen Khachanov needed a little shy of three hours to beat Alex de Minaur, his dubious reward a second-round clash with Novak Djokovic as the world number one continues his return to the Tour following his controversial Australian Open absence.

Andy Murray will face the surprise package of last year's Australian Open in Saturday's final of the Sydney Classic.

Blocking Murray's way to a first ATP Tour title since October 2019 will be Russian player Aslan Karatsev, whose gritty win over Dan Evans prevented an all-British final.

Evans won a marathon tie-break in the second set of that encounter but could not maintain the level as he lost out 6-3 6-7 (13-15) 6-3 to a player who caused a sensation by reaching the 2021 Australian Open semi-finals.

It was also a case of digging deep for Murray, who picked up a stellar win over American Reilly Opelka, triumphing 6-7 (6-8) 6-4 6-4 against the fourth seed and world number 25. Murray is ranked down at number 135, but this strong week has provided evidence he still belongs at a much higher level.

Three years have passed since Murray came to Australia and indicated he was close to retirement due to hip trouble. He has battled back against the odds to stay active, but his lone ATP singles final appearance since that point came at the 2019 European Open in Antwerp, where he beat Stan Wawrinka to land a surprise title.

Now he is back in another title match, for what will be just his fourth singles final on the main tour since the end of the 2016 season, when he reached world number one status.

Murray rifled 16 aces and no double faults, winning an impressive 88 per cent of points when he landed his first ball in court, and his serve was not broken at any point by Opelka.

He has 46 singles titles and dearly wants to reach 50 before calling it a day, with a glorious chance to land a 47th coming up on Saturday.

Karatsev, the world number 20, is not a player that Murray would underestimate. He was ranked 114th and largely unknown before going on his run to the final four in Melbourne last February, but he has since pushed on and should provide a stiff test for three-time major winner Murray.

"It's already been a great week for me, big progress from anything I've done in the last year or so, to string four matches together like this and against top players in Basilashvili and Opelka," said Murray. "I'll go for 47 tomorrow. It's been a good week, I've played better with each match, so hopefully I'll step it up again."

At the Adelaide International 2 event, Australian wildcard Thanasi Kokkinakis produced a stunning semi-final win over fourth seed Marin Cilic, battling to a 6-2 3-6 7-6 (12-10) victory over the former US Open champion, teeing up a shot at Frenchman Arthur Rinderknech in the title match.

Felix Auger-Aliassime pulled off a terrific win over Alexander Zverev to carry Canada through to the ATP Cup semi-finals.

After Great Britain beat the United States 2-1 earlier to stake a claim for a last-four spot, Canada's singles players rose to the challenge to see off Germany.

That meant disappointment for Dan Evans and the British team, with Canada progressing to a clash with Russia as winners of Group C.

Denis Shapovalov got the better of Jan-Lennard Struff in a tight tussle, the world number 14 beating 51st-ranked Struff 7-6 (7-5) 4-6 6-3, giving Auger-Aliassime a swing at Olympic Games and ATP Finals champion Zverev before a possible doubles decider.

The world number 11 duly got the better of third-ranked Zverev by a similar score to the opening singles rubber, winning 75 per cent of first-serve points as he came through 6-4 4-6 6-3 late at night in Sydney.

Great Britain had impressed in edging out the US team, with Dan Evans beating John Isner and then teaming up with Jamie Murray to see off Isner and Taylor Fritz 6-7 (3-7) 7-5 10-8 in a dramatic doubles decider. Fritz beat Cameron Norrie in the second singles rubber.

Daniil Medvedev played a pivotal role as Russia wrapped up a perfect 3-0 match record in Group B, beating Italy 2-1 to nail down their semi-final place.

Defending champions Russia, who also won the Davis Cup last year, were on the back foot early on against Italy after Jannik Sinner beat Roman Safiullin, but US Open champion Medvedev ground out a 6-2 6-7 (5-7) 6-4 win over Matteo Berrettini to take the match – and the battle for top spot in the group – down to a doubles decider.

Medvedev and Safiullin were given a stiff test by their singles foes on the doubles court but had just enough to beat Berrettini and Sinner 7-5 4-6 10-5.

Top seed Daniil Medvedev made quick work of Mackenzie McDonald in his opening match at the Indian Wells Masters, cruising to a 6-4 6-2 victory on Saturday.

Medvedev – the US Open champion – has lost only three of his last 41 sets, and has never dropped one to McDonald in five career meetings with the American as he maintained his red-hot form. 

Russian star Medvedev is now 37-5 on hardcourts this year and appears well-positioned to make it past the third round of the ATP Masters 1000 tournament for the first time as he awaits Filip Krajinovic.

"I'm actually really pleased, because usually I haven’t played well in Indian Wells and I haven’t been playing that well in practices before [the tournament]," Medvedev said in his on-court interview. "[I am] really happy with my performance. That’s the most important [thing] no matter how I played before the tournament."

RUBLEV ROLLS PAST TABERNER

Medvedev's countryman Andrey Rublev closed out the night session with a 6-3 6-4 defeat of Carlos Taberner, who was facing a top-10 opponent for the first time. 

Fourth seed and world number five Rublev won 66 per cent of points on his first serve and hit 30 winners to Taberner's 12. 

Rublev improved to 47-16 this season, 31-9 on hard courts, and will face Tommy Paul in the third round. 

SHAPOVALOV WINS IN NEAR-WALKOVER

Most of the seeded players in action had an easy time of it, none more so than Canadian ninth seed Denis Shapovalov.

Shapovalov's opponent and countryman Vasek Pospisil retired with an apparent back injury after dropping the first three games of the match. 

Sixth seed Casper Ruud blew past Roberto Carballes Baena 6-1 6-2, while eighth seed Hubert Hurkacz downed Alexei Popyrin 6-1 7-5. 

Diego Schwartzman had to work harder to advance, the 11th seed outlasting qualifier Maxime Cressy 6-2 3-6 7-5. 

Top-ranked American Reilly Opelka, the 16th seed, beat Taro Daniel 7-5 6-3 for his first main-draw victory at Indian Wells in four attempts. 

Daniel Evans also went the distance to defeat Kei Nishikori 4-6 6-3 6-4, while former world number three Grigor Dimitrov, 2021 Australian Open semi-finalist Aslan Karatsev and Frances Tiafoe were among the other players to advance.

Andy Murray's stay in San Diego was short-lived, as the veteran fell to second seed Casper Ruud in straight sets Thursday. 

World number 10 Ruud prevailed 7-5 6-4 over the three-time grand slam winner, rolling to victory after a shaky start. 

Murray broke Ruud in the 22-year-old's second service game of the match, but could not maintain the advantage as Ruud converted five of six break points in the match. 

Ruud will face ninth seed Lorenzo Sonego, who defeated Sebastian Korda 6-4 6-3, saving six of seven break points against his own serve while converting all three of his chances on Korda's. 

Fourth seed Denis Shapovalov defeated Taylor Fritz 7-6 (9-7) 6-2, saving six set points in the process. 

The Canadian moves on to a quarter-final meeting with Cameron Norrie, who downed Daniel Evans 7-6 (7-3) 6-3. 

Grigor Dimitrov dominated August Holmgren 6-1 6-1 in 56 minutes, winning 83 per cent of his service points.

Dimitrov next faces Aslan Karatsev, who rallied to upset fifth seed Hubert Hurkacz 5-7 6-4 6-2. 

Top seed Andrey Rublev brushed aside Brandon Nakashima in just over an hour to clinch a spot in the San Diego Open quarter-finals.

Rublev – the world number five – won 6-2 6-1 over local 20-year-old Nakashima at the ATP 250 tournament on Wednesday.

Nakashima claimed only two of 18 second serve points for the match, with Rublev breaking him six times and triumphing in one hour, two minutes midweek.

The result improves 2021 Australian Open quarter-finalist Rublev's record to 45-15 this calendar year.

Rublev will take on sixth seed Diego Schwartzman, who rallied to defeat Lloyd Harris 4-6 6-3 6-2 in San Diego.

Fifth seed Hubert Hurkacz moved into the next round with a 7-6 (7-2) 6-1 victory over Australian qualifier Alex Bolt.

Hurkacz will face Russian and 2021 Australian Open semi-finalist Aslan Karatsev in the round of 16.

Daniel Evans – the eighth seed – overcame former Wimbledon and US Open runner-up Kevin Anderson 7-6 (13-11) 7-5 after more than two hours on court.

Evans will meet countryman Cam Norrie next.

Daniil Medvedev said "it's tough to beat me" as the confident and in-form world number two took another step towards his maiden grand slam crown at the US Open.

Medvedev advanced to the quarter-finals with a comfortable 6-3 6-4 6-3 victory over 24th seed Dan Evans in New York on Sunday.

US Open finalist in 2019 and Australian Open runner-up this year, Russian star Medvedev is yet to drop a set at Flushing Meadows this week.

As Dutch qualifier Botic Van De Zandschulp awaits, Medvedev discussed expectations at the US Open in pursuit of his first major title.

"I always say I take it match by match," Medvedev told reporters after hitting 42 winners in one hour, 43 minutes. "You can lose first round, you can lose final. If I play good, I know what I'm capable of. It's tough to beat me.

"In Wimbledon, I was honest, I lost against a great player, Hubert is playing great. I think he's on the rise. He's going to be even better ranked and maybe he's gonna go further in slams. He beat Roger [Federer] after me.

"But again, I was not talking about match itself where the loss was okay, I would say. I was talking about the result in general, and fourth round is not enough for number two in the world, especially I like grass more than clay, so maybe on clay I would not say this.

"Yeah, it's the same every tournament. If you're top seed, if you are not in the final, let's say Cincinnati, I lost against Rublev, brutal match, really strong play from him. But if you talk about the result itself, semi-final was not good enough.

"There is not much to add. I want to win every tournament I play in, without putting pressure on myself. Because again, I know how to win matches, and I know sometimes why I lose them, so that's just learning and being better for the next time."

Medvedev is 31-5 on hard courts in 2021 and 162-61 in his career, while he has won 11 of his 12 ATP titles on hard courts.

The 25-year-old owns a 17-4 record (80.95 per cent) at the US Open – his most wins and highest win percentage at a grand slam event.

"Feeling great before the second week," Medvedev said. "Feeling great with my tennis, my mental, my physical. Just looking forward."

Medvedev, who lost a thrilling US Open final to Rafael Nadal two years ago, added: "Now I just want to make it to the finals again to have another thing to remember and hopefully a better one."

Top seed Matteo Berrettini has his sights set on the Queen's Club Championships title after beating Dan Evans in the quarter-finals.

After a delay of more than four hours because of rain in London, Berrettini overcame Evans 7-6 (7-5) 6-3 to reach his third ATP grass-court semi-final.

The Italian hit 13 aces and won 81 per cent of his first-serve points against Evans to set up a last-four clash with Alex de Minaur. 

Berrettini improved his win-loss record to 24-6 for the season and laid out his ambition to walk away from the tournament with the trophy.

"I didn't serve that well, but I was returning well and I just played better in the last few points of the tie-break," he said.

"After that, I felt more confident. The conditions were really tough, windy and cold, so I took time to adapt a little bit. I am pretty happy with my performance.

"The court condition was really good. I expected slippery conditions, but it was like yesterday.

"I came here to win the tournament, that is my goal. Now I am two steps away. I am happy with the way I am playing, and my mental attitude is really good."

Up next for Berrettini is Australian De Minaur, who came from behind to defeat Marin Cilic 3-6 6-3 6-4.

The 22-year-old won 73 per cent (22/30) of his second-serve points and saved six of the seven break points he faced as he moved to 16-12 for the season.

In the battle of the British players, Cameron Norrie beat Jack Draper 6-3 6-3, while Denis Shapovalov was leading Frances Tiafoe 6-3 when their match was suspended due to fading light. They will resume on Saturday.

At the Halle Open, Andrey Rublev reached his sixth ATP Tour semi-final of the year thanks to a 7-6 (7-4) 6-2 win over 2011 champion Philipp Kohlschreiber.

"I am happy with my performance to reach the semi-finals for the first time," Rublev said. "The first set was really tough. He was 3-0 up in the tie-break and I came back, which was the key.

"After the first set, I think he mentally went down and I was pumped up. I hit a couple of good returns in the first game of the second set."

Russian Rublev will face Nikoloz Basilashvili in the last four after the Georgian defeated Lloyd Harris 6-4 7-6 (7-5). 

In the day's other quarter-finals, Felix Auger-Aliassime beat Marcos Giron 6-3 6-2 and Ugo Humbert overcame Sebastian Korda 6-2 6-7 (5-7) 6-4.

Top seed Matteo Berrettini beat Andy Murray to reach the quarter-finals at Queen's Club and Ugo Humbert upset Alexander Zverev at the Halle Open on Thursday.

Murray, a five-time champion at Queen's, was beaten 6-3 6-3 by Italian Berrettini as the three-time grand slam champion struggled a day on from being given a Wimbledon wildcard.

The former world number one beat Benoit Paire in his first ATP Tour singles match since March on Tuesday, but the 34-year-old revealed he is still being troubled by a groin injury after his loss to Berrettini and knows he must raise his game.

Murray said: "I actually felt my movement was actually quite good for both of the matches. My tennis today was not very good. That's the thing that I'll need to improve the most.

"Then there is still a slight niggle in the groin, so [I have] to try to get rid of that discomfort between now and Wimbledon. I need to be playing points, basically. I played two sets in preparation for this event.

"I do feel like I genuinely have been hitting the ball well in practice, but then like today when you're under a bit more pressure and stuff and you're having to make very split-second decisions when you're on the court, if the guy is serving 140 miles an hour, like, it's difficult to prepare for that."

Dan Evans made history earlier in the day, getting the better of Adrian Mannarino 6-4 7-6 (9-7).

With Jack Draper and Cameron Norrie having already progressed, Evans' win ensured there will be three Britons in the singles quarter-finals for the first time in the Open Era.

Feliciano Lopez will not retain his title in London after the Spaniard went down 6-2 6-3 to second seed Denis Shapovalov. Spanish veteran Lopez won in 2019, with last year's tournament cancelled due to the pandemic.

There will be no glory on home soil in Halle for German Zverev, who was taken out 7-6 (7-4) 3-6 6-3 by unseeded Frenchman Humbert.

Humbert has now beaten a top-10 player on every surface, with Zverev serving 20 aces but bowing out after his 22-year-old opponent claimed the only break of the final set.

Sebastian Korda battled past Kei Nishikori 2-6 6-3 7-5 in Halle, while Lloyd Harris also moved into the last eight at Lukas Lacko's expense.