Feliciano Lopez reached the milestone of 500 ATP Tour wins with a comeback victory over Karen Khachanov at the Mallorca Championships.

Lopez, who turns 40 in September, prevailed 4-6 6-2 6-4 against the sixth seed.

He is the 10th active player to reach 500 wins, after Roger Federer, Rafael Nadal, Novak Djokovic, Andy Murray, Richard Gasquet, Fernando Verdasco, Marin Cilic, Stan Wawrinka and Tommy Robredo.

"More than the 500 wins, the important thing to me is the chance to keep playing in these kinds of tournaments and to keep being competitive," Lopez told ATPTour.com.

"I didn’t expect to be able to play at the level I am on the ATP Tour at 40 years of age, which I will be in September."

Spanish veteran Lopez would have expected to be taking on Dominic Thiem next, but the world number five retired due to a wrist injury when 5-2 to the good in the opening set against Adrian Mannarino.

"It's nice for me to be in the quarter-finals, but winning this way is not so cool. I really like Dominic, he's such a nice guy and I hope he will be feeling better soon," Mannarino said. "I hope it is not so serious, especially right before Wimbledon."

Elsewhere on the Balearic island, top seed Daniil Medvedev breezed past Corentin Moutet 6-4 6-2, while Casper Ruud defeated Tennys Sandgren in straight sets.

At the Viking International in Eastbourne, there were mixed fortunes for Lopez's countrymen Alejandro Davidovich Fokina and Albert Ramos-Vinolas.

Fokina, seeded sixth, saw off Mikael Ymer 7-5 6-1, but number seven seed Ramos-Vinolas fell 6-4 6-3 to Emil Ruusuvuori.

Alexander Bublik defeated fellow Kazakh Mikhail Kukushkin is straight sets, while Jo-Wilfred Tsonga went down in similar fashion against Egor Gerasimov.

Nikoloz Basilashvili won a fifth ATP Tour title as he triumphed at the BMW Open on Sunday.

The Georgian completed an impressive week in Munich by beating Jan-Lennard Struff 6-4 7-6 (7-5) to clinch the trophy without dropping a set in his five matches.

The win continued what has been a solid 2021 for Basilashvili, who won the title in Doha in March after defeating Roger Federer in his second match following his return from injury.

After retiring from his opening match in Monte Carlo last month before losing to Jeremy Chardy in Barcelona, the world number 35 had looked in fine form in Munich before battling to victory against Struff in just under 86 minutes.

"It wasn't easy and I was super-tight at the end," said Basilashvili. "It was very difficult. It's never easy playing Jan, he's a very big fighter and serves really well.

"I am super happy. It seems like German conditions suit me. This is my fifth [ATP Tour] title and it will give me confidence for the upcoming tournaments."

At the Estoril Open, Albert Ramos-Vinolas emerged victorious from a marathon final against Cameron Norrie.

The 33-year-old was a set and a break down but rallied to win 4-6 6-3 7-6 (7-3) in two hours and 44 minutes in Portugal.

It was the Spaniard's third Tour title and took him to a 16-5 record on clay this season. He has at least seven more wins on the surface than any other ATP player this season.

Novak Djokovic will tackle teenage rising star Jannik Sinner for the first time in a tantalising clash of tennis generations on Wednesday at the Monte Carlo Masters.

World number one Djokovic is returning to action this week, having taken time away from the tour since banking an 18th grand slam title by winning the Australian Open in February.

He received a first-round bye, but waiting for him in the last 32 is Sinner, who on Tuesday saw off 2017 Monte Carlo runner-up Albert Ramos-Vinolas 6-3 6-4, again illustrating the 19-year-old Italian's great potential.

World number 22 Sinner is the only teenager ranked inside the top 80 in the men's game and is coming off his first run to a Masters final, at the Miami Open.

The switch from hard courts to clay is one that Sinner is having to deal with, and seeing off a specialist on the surface in round one represents an impressive start, although facing two-time former champion Djokovic will be a step up.

"It's always good for me to see what I can do on clay," Sinner said, quoted on the ATP website. "Obviously, I am not in the best form on clay now for the first week.

"But I think today was a solid match from my side. It was not easy. He's not giving [away] one point, so you have to stay there the whole match. I think I played a good match from my side."

Greek fourth seed Stefanos Tsitsipas reached the last 16 with a 6-3 6-4 win over Russian Aslan Karatsev, but there was disappointment at the same stage for Italian eighth seed Matteo Berrettini, beaten 7-5 6-3 by Spain's Alejandro Davidovich Fokina. Those were the only second-round matches of the day.

Surprise Miami champion Hubert Hurkacz made a winning start, battling to a 6-3 3-6 6-3 first-round success against Italian qualifier Thomas Fabbiano to reach round two.

Roberto Bautista Agut, Grigor Dimitrov, Pablo Carreno Busta and Fabio Fognini each booked places in round two thanks to straight-sets wins.

Qualifier Federico Delbonis was a 7-5 6-1 victor over France's Adrian Mannarino, meaning the Argentinian faces the ultimate test in clay-court tennis next, a tussle with Rafael Nadal, the 11-time former champion in Monte Carlo.

Nadal has won all four of their previous matches, and their fifth encounter will immediately follow the Djokovic-Sinner match on Wednesday.

Top seed Pablo Carreno Busta led a clean sweep for home players to head up an all-Spanish semi-final slate at the Andalucia Open, where teenage sensation Carlos Alcaraz made history.

Carreno Busta demolished seventh seed Soonwoo Kwon 6-4 6-0, while Casper Ruud was stunned in straight sets by wildcard Alcaraz.

The 17-year-old backed up his victory over the veteran Feliciano Lopez in style, becoming the youngest ATP Tour semi-finalist since Alexander Zverev at Hamburg in 2014 with a 6-2 6-4 win.

Albert Ramos-Vinolas will face Carreno Busta after beating Norbert Gombos 6-7 (4-7) 7-5 6-4, while Alcarez is next on the agenda for compatriot Jaume Munar, who was taken the distance by Ilya Ivashka having overcome second seed Fabio Fognini on Thursday.

Taylor Fritz continued his solid form this season with a straight sets victory over Aljaz Bedene to reach the semi-finals of Sardegna Open.

Fritz is playing as the US number one for the first time in Cagliari this week and he made light work of Bedene, prevailing 6-3 6-4 to book a showdown with third seed Lorenzo Sonego, who beat Yannick Hanfmann 3-6 7-6 (8-6) 6-3 despite being 3-5 down in the second.

Seeded second and ranked 30 in the world, Fitz improved his 2021 record to 11-5 and will look to avenge a defeat in his only other meeting with Sonego on clay, when he lost at Roland Garros last year.

Lorenzo Musetti thrilled as he saved four match points to sink top seed Dan Evans on Thursday but bowed out after another epic, losing to Serbia's Laslo Djere 6-4 4-6 6-2 in two hours and 21 minutes.

Djere, who beat sixth seen John Millman en route to the quarter-finals, will face Nikoloz Basilashvili after the battle between seeds four and five ended 7-5 4-6 6-3 in the Georgian's favour.

Pablo Carreno Busta got his quest to win a maiden ATP Tour title in his homeland under way with a straight-sets defeat of Mario Vilella Martinez in the Andalucia Open.

Top seed Carreno Busta needed an hour and 38 minutes to dispatch his fellow Spaniard 7-6 (7-2) 6-3 in Marbella on Wednesday.

Carreno Busta won 73 per cent of points on his first serve and saved the only two break points he faced to set up a quarter-final against Soonwoo Kwon, who beat Facundo Bagnis 6-1 6-3.

Albert Ramos-Vinolas was another home contender to progress, getting the better of Ricardas Berankis 6-3 4-6 6-3, while Norbert Gombos ousted eighth seed Federico Delbonis 5-7 7-6 (7-4) 7-6 (7-1).

There were no surprises in the Sardegna Open, where all three seeds in action moved into the last eight.

Taylor Fritz, the second seed, saw the back of Andrej Martin 6-2 7-6 (7-4) to set up a meeting with Aljaz Bedene, who beat Egor Gerasimov 6-4 7-6 (7-5).

Fifth seed Jan-Lennard Struff needed only 81 minutes to defeat qualifier Liam Broady 6-4 6-2, while Nikoloz Basilashvili rallied from a set – and five match points – down to see off Jozef Kovalik 4-6 6-4 7-5.

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