Roberto Bautista Agut followed two sprints with a gruelling slog as he battled past Karen Khachanov to reach the final of the Qatar Open.

Spanish second seed Bautista Agut had dashed past Andy Murray and Alejandro Davidovich Fokina for the loss of just three games in Doha, but Khachanov proved far more obdurate.

After a slow start, eventually Bautista Agut picked up the pace and emerged a 2-6 6-3 7-5 winner in two hours and 24 minutes of toil, earning a shot at Georgia's Nikoloz Basilashvili in Saturday's final.

Bautista Agut praised Russian Khachanov for making him scrap for the win.

"He was playing very fast," said Bautista Agut, quoted on the ATP website. "He was playing very solidly, he was defending very well and he hit many unbelievable passing shots. I had to play incredibly well tonight. I enjoyed tonight so much."

Third seed Basilashvili is the defending champion this week and made light work of France's Arthur Rinderknech, tying up a 6-4 6-2 victory.

In Marseille, Greek top seed Stefanos Tsitsipas was stunned by Russian qualifier Roman Safiullin in the Open 13 quarter-finals. World number 163 Safiullin had a staggering 13 break points against the under-performing Tsitsipas serve, and although 11 of those were saved, the two that were not decided the match.

Safiullin, for his part, faced one break point and saved it on the way to a 6-4 6-4 victory. He made his presence felt at the ATP Cup in Australia at the start of the year and, although results have been disappointing since, the 24-year-old is doing well again in France this week.

Next for Safiullin will be last week's Rotterdam champion Felix Auger-Aliassime, who saw off Belarusian Ilya Ivashka 6-3 6-4 in the last match of the day. After losing his first eight finals on the ATP Tour, Auger-Aliassime may well be closing in on a second title in eight days.

Saturday's other semi-final will see Russian second seed Andrey Rublev tackle Frenchman Benjamin Bonzi, who reached the last four of a main-tour event for the first time by crushing Aslan Karatsev 6-1 6-3.

Rublev dug deep to edge out French wildcard and former top-10 player Lucas Pouille 6-3 1-6 6-2.

Favourites Reilly Opelka and Grigor Dimitrov joined top seed Cameron Norrie in the quarter-finals of the Delray Beach Open after victories on Thursday.

With Norrie having already set up a quarter-final against last year's runner-up Sebastian Korda, the Briton was joined in the last eight by the second and third seeds. 

Grigor Dimitrov defeated Mitchell Krueger to mark his first appearance since a disappointing second-round exit at the Australian Open in style.

The Bulgarian won 7-6 (7-4) 6-3, with Serena and Venus Williams watching on from the crowd in far from ideal conditions in Florida.

"It's always very tough [in your opening match], especially playing the last match on," Dimitrov said.

"I've been here for a week already and I was eager to get out there and play. Today was just a match I had to get through. Very tough conditions: rain, wind, cold, hot. It is what it is, and you've got to deal with it."

Opelka, who won the tournament in 2020, went the distance against fellow American Jack Sock, eventually prevailing 6-7 (6-8) 7-6 (7-4) 6-1. 

He will face Adrian Mannarino in the last eight, after the Frenchman's 6-4 2-6 7-5 defeat of Brandon Nakashima. Dimitrov will play Australian John Millman.

At the Rio Open, only two of the four scheduled matches were completed due to rain.

Qualifier Miomir Kecmanovic dispatched sixth seed Lorenzo Sonego 7-5 6-4, while Francisco Cerundolo overcame Roberto Carballes Baena.

Top seed Matteo Berrettini's clash with Brazilian Thiago Monteiro was pushed back to Friday, while Carlos Alcaraz will resume his match against Federico Delbonis in a strong position in the first set.

Denis Shapovalov crashed out of the Qatar Open after losing in straight sets to France's Arthur Rinderknech in their quarter-final on Thursday.

The top-seeded Canadian lost in just an hour and 20 minutes as Rinderknech sealed a 6-4 6-4 victory to seal his place in the semi-finals in Doha.

Shapovalov struggled throughout, making nine double faults and having to face 10 break points, of which he managed to save eight.

Rinderknech will now face Nikoloz Basilashvili after the Georgian fought back to beat Marton Fucsovics 1-6 6-3 7-5.

The other semi-final will see Karen Khachanov take on Roberto Bautista Agut, with the Russian also coming from a set down in beating Marin Cilic 3-6 6-3 6-4.

Bautista Agut followed up Wednesday's 6-0 6-1 victory against Andy Murray by again winning comfortably against fellow Spaniard Alejandro Davidovich Fokina, scoring a 6-1 6-1 success.

The number two seed won 74 per cent of points when landing his first serve as he sealed victory in an hour and 17 minutes.

At the Open 13 in Marseille, Rotterdam champion Felix Auger-Aliassime increased his winning streak to six matches after beating French veteran Jo-Wilfried Tsonga 7-6 (7-3) 6-2 to head through to the quarter-finals.

"It was a special moment," Auger-Aliassime said after his win. "When the match was coming to the end, I knew it was going to be a special moment, a full-circle moment. He was my top idol growing up and I saw myself in him at times."

Auger-Aliassime will play world number 49 Ilya Ivashka next, while top seed Stefanos Tsitsipas also went through after a 6-3 7-6 (7-4) win against Hugo Gaston. The Greek star will play Russian Roman Safiullin in the last eight.

Ninth seed Benjamin Bonzi beat fellow Frenchman Pierre-Hugues Herbert 6-4 6-3 and will go up against Aslan Karatsev in the next round, while Lucas Pouille overcame Radu Albot 6-3 3-6 7-6 (7-2) and will tackle Andrey Rublev next.

Diego Schwartzman felt he played "an almost perfect match" to overcome Pedro Martinez in straight sets and reach the quarter-finals of the Rio Open.

The third seed advanced with a 6-1 6-1 victory, though that does not quite tell the whole story as the second game of the first set lasted a mammoth 24 minutes and 40 seconds.

Martinez saved eight break points in that lengthy game before finally being outdone by Schwartzman, who will now face another Spaniard in Pablo Andujar.

Incredibly, Martinez won 31 points in the first set but just one game.

"It was unbelievable," Schwartzman said. "This was probably the longest game in the history of the tournament 

"I don't remember anything like this before. I played an almost perfect match, I played against an opponent that had as much confidence as me."

Andujar beat Albert Ramos-Vinolas 7-5 5-7 6-3, while fourth seed Pablo Carreno-Busta lost 5-7 6-4 6-3 to Fabio Fognini in the shock of the day.

Federico Coria awaits Fognini after following up his surprise win over defending champion Cristian Garin with a 7-6 (7-2) 4-6 6-4 victory against Fernando Verdasco.

At the Delray Beach Open, top seed Cameron Norrie beat Oscar Otte 6-3 7-5 and will face Sebastian Korda, who saw off Andreas Seppi 7-5 6-3, for a place in the semi-finals.

Tommy Paul and Stefan Kozlov are also through to the final eight in Florida after beating Denis Istomin and Steve Johnson respectively in straight sets.

Andy Murray suffered one of the heaviest losses of his career in the second round of the Qatar Open, while Andrey Rublev escaped an early exit at the Open 13. 

Former world number one Murray went down 6-0 6-1 to last year's runner-up Roberto Bautista Agut in Doha on Wednesday. 

It was just the fourth occasion in which the three-time major champion has lost a match while winning only one game or fewer in his career – the last time being a defeat by the same scoreline to Roger Federer at the ATP Finals in 2014. 

Murray's fellow Briton Dan Evans also endured a second-round loss, going down 4-6 7-5 6-4 to Alejandro Davidovich Fokina – Bautista Agut's next opponent. 

Denis Shapovalov bounced back from his first-round loss to Jiri Lehecka in Rotterdam last week by dropping just eight points on serve as he claimed a 6-4 6-0 victory over Alex Molcan inside 52 minutes. 

Next up for the Canadian will be Arthur Rinderknech after the Frenchman came from a set down to defeat seventh seed Alexander Bublik 6-7 (5-7) 6-1 6-4. 

Nikoloz Basilashvili faced little trouble in overcoming Elias Ymer 6-4 7-5 and his reward is a quarter-final against Marton Fucsovics, who got the better of Kwon Soon-woo. 

Karen Khachanov and Marin Cilic will meet in the last eight after they respectively eliminated Emil Ruusuvuori and Botic van de Zandschulp. 

In Marseille, second seed Rublev was made to work hard for a place in the Open 13 quarter-finals by home hope Richard Gasquet. 

Gasquet went a break up in the third set and, after surrendering his advantage, stopped Rublev serving out the match to force a tie-break. 

However, the world number seven did not waste his next opportunity as he sealed a 4-6 6-4 7-6 (7-3) success. 

Aslan Karatsev also booked his place in the last eight, while there were wins for Frenchmen Benjamin Bonzi and Lucas Pouille too. 

Defending champion Cristian Garin was victim of the biggest shock of Tuesday's play at the Rio Open.

Fifth seed Garin – winner of the most recent edition in 2020 – exited a second consecutive tournament at the first-round stage after he was humbled by Federico Coria.

Coria had defeated the fifth seed, Dusan Lajovic, at last week's Argentina Open, too, but was particularly impressive on Tuesday.

A stunning 6-2 6-0 win was sealed in an hour and 16 minutes.

Coria fended off two break points midway through the first set and then won the remaining nine games in succession in a dominant victory.

Garin was the only seed to lose in Brazil, however, as Lorenzo Sonego was on the right side of a 6-2 6-0 scoreline against 2019 winner Laslo Djere.

Fabio Fognini also advanced in straight sets, while Spanish pair Albert Ramos-Vinolas and Fernando Verdasco similarly eased through.

At the Delray Beach Open, 2021 runner-up Sebastian Korda defeated Thanasi Kokkinakis in his first match since winning the Australian Open doubles title with Nick Kyrgios.

Former champion Sam Querrey came up short against Denis Istomin.

Andy Murray made a winning start at the Qatar Open after defeating Taro Daniel 6-2 6-2 in Doha.

The three-time grand slam winner was beaten in straight sets when he faced Daniel in the second round at the Australian Open last month.

But he avenged that defeat with a dominant display against the world number 110 that saw him prevail in one hour and 20 minutes.

Murray boasts an impressive record at the ATP 250 event, lifting the trophy in 2008 and 2009 while reaching a further two finals (2007 and 2017).

And the 34-year-old wildcard will face second seed Roberto Bautista Agut in round two.

"Taro played very well in Australia," Murray said. "He had a very good run there and was too good for me there. 

"I tried to be the one dictating from the first point, and I thought I did that well. It was one of the better matches I've played in recent months.

"Obviously, the results from years ago aren't going to affect the results this week.

"But what it tells me is that the conditions here are good for my game, so if I can play to a good level, the courts are going to suit me here, and I'll make it difficult for everyone I play against."

Elsewhere, seventh seed Alexander Bublik hit 25 winners – including seven aces – in a 6-2 6-4 victory over Slovakia's Jozef Kovalik.

However, there was no joy for Lloyd Harris; the eighth seed was beaten in straight sets by Hungarian Marton Fucsovics for the second year running.

Over at Open 13 in Marseille, three-time winner Jo-Wilfried Tsonga overcame fellow wildcard Gilles Simon 6-2 6-4 in the battle of the players boasting five titles between them at the event.

But seventh seed Alexei Popyrin lost out in a deciding-set tie-break to world number 163 Roman Safiullin.

Novak Djokovic has said missing grand slams including the French Open and Wimbledon will be "the price I am willing to pay" for resisting the COVID-19 vaccine.

Last month, the world number one and 20-time grand slam winner was deported from Australia on the eve of the Australian Open after his entry visa to the country was cancelled.

That stemmed from Djokovic refusing to join the overwhelming majority of fellow tennis stars in being vaccinated against coronavirus, and amid controversy over how he handled getting the virus himself in December.

In a new interview with the BBC, Djokovic said he was prioritising his right to choose what to put into his body above his sporting ambitions.

The 34-year-old Serbian declared his stance is likely to keep him sidelined for "most of the tournaments" at present.

Djokovic is set to make his return to the court at the Dubai Duty Free Tennis Championships later this month, with vaccination not a requirement. He has been included on the entry list for next month's Indian Wells Open, but that is a tournament he may have to sit out.

He confirmed in the BBC interview that he has still yet to be vaccinated, though did not entirely rule out the prospect in the future.

"I have not," he said. "I understand and support fully the freedom to choose whether you want to get vaccinated or not."

Prior to entering Australia, where he was obliged to confirm his status, it was only widely assumed that Djokovic had not been inoculated.

Now he is keen to "speak up ... and justify certain things", adding: "So I was never against vaccination. I understand that globally everyone is trying to put a big effort into handling this virus and seeing hopefully an end soon to this virus.

"And vaccinations are probably the biggest effort that was made on behalf of the planet. I fully respect that, but I've always represented and always supported the freedom to choose what you put into your body. For me that is essential. It's really the principle of understanding what is right and what is wrong for you.

"And me, as an elite professional athlete, I've always carefully reviewed and assessed everything that comes in, from the supplements, food, the water that I drink or sports drinks. Anything really that comes into my body as a fuel.

"Based on all the information that I got, I decided not to take the vaccine as of today. I keep my mind open because we are all trying to find collectively a best possible solution to end COVID. Nobody really wants to be in this kind of situation that we've been in collectively for two years."

Djokovic is the reigning French Open and Wimbledon champion and, after Rafael Nadal's Australian Open triumph, he has been bumped down to joint second on the all-time men's grand slam list. Missing majors at this stage of his career could be a crushing blow to Djokovic's hopes of finishing top of that pile.

"I'm part of a very global sport that is played every single week in a different location, so I understand the consequences of my decision, and one of the consequences of my decision was not going to Australia, and I was prepared not to go," Djokovic said.

"I understand that not being vaccinated today I am unable to travel to most of the tournaments at the moment. That is the price I am willing to pay."

He looked to disassociate himself from the anti-vax community by saying he had "never said I am part of that movement" and declaring that was a "wrong conclusion" to draw.

At the same time, Djokovic concurred when asked if he was willing to sacrifice the chance to be seen as the greatest player of all time, and to travel to Roland Garros and the All England Club this year.

"Because the principles of decision-making on my body are more important than any title or anything else. I'm trying to be in tune with my body as much as I possibly can," Djokovic said.

"I say that everyone has a right to choose to act or say whatever they feel is appropriate for them."

Teenage seventh seed Carlos Alcaraz fought back from a poor set to win 2-6 6-2 6-1 over fellow Spaniard Jaume Munar at the Rio Open on Monday.

The 18-year-old struggled for rhythm in the opening set but showed composure to respond by breaking Munar early in the second set and dominating from there.

Alcaraz took the victory in two hours and 15 minutes, saving 10 of 13 break points across the match, while dropping only three games in the second and third sets.

Spaniard Pedro Martinez set up a second-round clash with third seed Diego Schwartzman after a 6-3 6-4 win over Shang Juncheng.

Pablo Andujar Alba also progressed 7-6 (7-2) 7-5 over Pablo Cuevas, while Serbian qualifier Meomir Kecmanovic accounted for local wildcard Felipe Meligeni Rodrigues Alves 6-3 6-0.

At the Delray Beach Open in Florida, Steve Johnson beat South African veteran Kevin Anderson in just over two hours, triumphing 6-2 6-7 (5-7) 6-2.

Oscar Otte got past Yoshihito Nishioka 7-6 (10-8) 6-3 to set up a second-round date with top seed Cameron Norrie, while there were only two breaks across the match as seventh seed Maxime Bressy was ousted by John Millman 6-7 (2-7) 7-6 (7-2) 7-6 (7-3).

Italian veteran Andreas Seppi beat German Peter Gojowczyk 7-5 6-4, while young American Brandon Nakashima comfortably handled Denis Kudla 6-1 6-1.

Dan Evans and Karen Khachanov made strong starts at the Qatar Open on Monday, while top seed Denis Shapovalov learned who his first opponent will be. 

After just over an hour and a half, fifth seed Evans sealed a 6-4 6-4 victory over Egor Gerasimov in their first meeting on the ATP Tour. 

Evans won 85 per cent of points behind his first serve and did not face a single break point as he advanced to the second round. Malek Jaziri or Alejandro Davidovich Fokina will be his next opponent. 

Following a tight opening set, Khachanov overcame Mackenzie McDonald 7-6 (7-3) 6-3 to continue his impressive form early in the 2022 season.

Alex Molcan came from a set down and navigated a second-set tie-break to defeat Chris O'Connell and earn a meeting with Shapovalov in the second round. 

At the Open 13 in Marseille, home hope Richard Gasquet overcame Mikael Ymer 6-4 7-5 to book a meeting with Andrey Rublev in the second round. There were also wins for Stefano Travaglia and Ilya Ivashka. 

Reilly Opelka rammed 16 aces past Jenson Brooksby on the way to victory in two tie-breaks in the all-American final of the Dallas Open.

In a battle between two of the United States' brightest young men's tennis talents, neither could find a way to break the other's serve.

That meant it came down to the shoot-out of the tie-break in each set, with Opelka sealing a 7-6 (7-5) 7-6 (7-3) victory in an hour and 51 minutes.

It gives the world number 23 a third ATP title of his career, all of which have been won in America. His previous successes came at Delray Beach and the New York Open.

This indoor showpiece on Sunday was just a second main-tour final for 54th-ranked Brooksby, a player who caught the eye in a breakout 2021 campaign, and he found Opelka's serve impenetrable, as has been the case for all-comers throughout the week.

Opelka faced just one break point in the title match, the first against his serve all week, but staved that off. He had five chances against the Brooksby serve but could also not take advantage.

Rather than power, Opelka finished off the match with finesse, hitting a backhand winner after a teasing exchange. He then described 21-year-old Brooksby as "a future top-10 player" after keeping the youngster waiting for his first ATP title.

Brooksby was ranked outside the top 300 this time last year and is poised for a first top-50 breakthrough.

The champion was delighted with his own game, with Opelka saying at the trophy presentation: "I thought I played very well under pressure, especially against a great player like Jenson.

"He makes you very uncomfortable and he took me out of my comfort zone a lot of the match today. I really had to play my best tennis to get by and I barely did."

Casper Ruud collected his sixth ATP Tour title as he battled past Diego Schwartzman to win the Argentina Open for a second time on Sunday.

Ruud managed five ATP titles in 2021 and followed that up with another one in the new season as he recovered from a first-set scare to overcome local favourite Schwartzman 5-7 6-2 6-3 in Buenos Aires.

The Norwegian extended his record at the tournament to 9-0, having already lifted the trophy in 2020, after negotiating past his Argentinian opponent in two hours and 35 minutes.

Ruud, who was the top seed, had not dropped a set all week on his way to the showpiece final, but he faltered in the first set as he spurned a break point at 5-4 up, with Schwartzman holding to make it 5-5 before subsequently claiming the opener.

Schwartzman repeated the feat in his first service game of the following set, staving off four break points, but Ruud rallied at 2-2 to claim four straight games and send the match to a decider.

Schwartzman was the defending champion after ending a 13-year wait for an Argentinian winner in Buenos Aires, though it was Ruud who lifted the trophy as he overcame an early break to extend his winning streak in ATP 250 events on clay to 18.

Felix Auger-Aliassime finally won a first ATP Tour title after impressively dealing with Stefanos Tsitsipas in straight sets in Rotterdam on Sunday.

The Canadian had lost all of his previous eight finals on the tour, not even clinching a set in any of them, but he found the winning formula this time as he beat Tsitsipas 6-4 6-2.

Auger-Aliassime made an emphatic start, breaking Tsitsipas in the very first game and from that point there was no looking back.

The 21-year-old's aggressive style of play had Tsitsipas on the back foot almost throughout and, after claiming the first set, he saw things out with admirable confidence.

He raced into a 5-1 lead in the second set and there were never any signs of nerves on his part, as he avoided facing a single break point over course of the full match.

Auger-Aliassime, who was beaten by Gael Monfils in the 2020 Rotterdam final, said: "It has not been the smoothest road since my first final three years ago.

"It is an amazing day for me to get my first title and especially here. I played my first ATP main draw here a couple of years ago [in 2018], so it is right I won my first title here.

"I have a lot of good memories playing here in front of you, so thank you for making it a special week for me that I will remember for the rest of my life.

"It is the happiest day of my career, and hopefully it is the first of many to come."

Tsitsipas accepted he lost to the better player on the day, bemoaning his struggles when serving.

The world number four won 74 per cent of points on his first serve and 33 per cent on his second – both figures were dwarfed by Auger-Aliassime's 93 per cent and 69 per cent, respectively.

"He played a really good match, producing really good shots and serving well the whole match," Tsitsipas said.

"I wasn't able to serve well at all today. He played very well."

The top two seeds Casper Ruud and Diego Schwartzman will face off in the Argentina Open final after the latter won two matches on Saturday to progress at his home event.

The Argentine world number 14 had to overcome countryman Francisco Cerundolo 6-3 2-6 5-7 earlier on Saturday after their quarter-final had been interrupted by rain on Friday evening.

The match was tied at 1-1 in the third set when rain intervened, with Schwartzman triumphing when play resumed to earn a semi-final date with third seed Lorenzo Sonego.

Schwartzman would later beat Sonego 7-5 3-6 6-2 in almost three hours on a busy day for the 2020 French Open semi-finalist.

World number eight Ruud progressed with a routine 6-3 6-3 victory over Argentine sixth seed Federico Delbonis.

At the Dallas Open semi-finals, Reilly Opelka and John Isner broke the record for the longest tiebreaker on the ATP Tour since 1990.

Second seed Opelka triumphed over fellow American Isner but it was not easy, winning 7-6 (9-7) 7-6 (24-22).

Opelka sent down 39-21 aces across the match, earning a spot in the final against fourth seed Jenson Brooksby who beat Marcos Giron 6-4 6-7 (4-7) 7-6 (7-5).

Stefanos Tsitsipas will face Felix Auger-Aliassime in the final of the ABN Amro World Tennis Tournament, after they prevailed in hard-fought semi-finals on a day of drama in Rotterdam. 

Top seed Tsitsipas faced a tough test against 20-year-old Czech qualifier Jiri Lehecka, whose dream run had included a shock win over world number 12 Denis Shapovalov.

The world number four was forced to battle back after losing the opening set, eventually beating the main-draw debutant 4-6 6-4 6-2.

Tsitsipas, whose last final appearance saw him blow a two-set lead over Novak Djokovic in the 2021 French Open showpiece, has yet to claim an ATP 500 title during his career, a record which he will now look to set straight against Auger-Aliassime. 

Currently ranked ninth in the world, the 21-year-old had to overcome a stern test of his own against defending champion Andrey Rublev, who sits two places higher in the ATP rankings, to reach the ninth final of his singles career.

After losing a thrilling first set in a tie-break, Auger-Aliassime roared back to claim a 6-7 (5-7) 6-4 6-2 win over the Russian, his first victory over Rublev in three career attempts.

Auger-Aliassime is chasing his first career title, after losing in the final of this same event against Gael Monfils in 2020.

The final will be Tsitsipas and Auger-Aliassime's eighth career meeting. The Greek has won the most recent five, including their only previous meeting on a hard indoor surface, in the final of 2020's Open 13 in Marseille.