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.

Rafael Nadal eased into the last 16 at the French Open as he cruised to a 6-3 6-2 6-4 victory over Botic van de Zandschulp on Friday.

Nadal breezed past Jordan Thompson and Corentin Moutet to reach the third round, where the Spaniard had few difficulties on Court Suzanne-Lenglen against world number 29 Van de Zandschulp.

The pair exchanged breaks to begin the match, but the 13-time winner at Roland Garros soon took control as he only lost four points on his service in the first set, all of which came in the first game.

Van de Zandschulp continued to struggle in the second set as Nadal triumphed in a lengthy third game to break again, before following suit in the Dutchman's next service to further his advantage en route to taking a two-set lead.

World number five Nadal again opened the third set by battling to break Van de Zandschulp twice and had the opportunity to go 5-0 up with points in hand.

The Dutchman fought back to win three straight games before claiming another, leaving the set finely poised at 5-4 to Nadal.

However, the 35-year-old Nadal regained his composure to wrap up victory and will next face Felix Auger-Aliassime, who defeated Filip Krajinovic.

Data Slam: Nadal on course for Djokovic meeting

Only Novak Djokovic (325) and Roger Federer (369) have more grand slam match wins than Nadal (301), who remains on course to meet the world number one in the quarter-final.

WINNERS/UNFORCED ERRORS
Nadal – 25/13
Van de Zandschulp – 19/31

ACES/DOUBLE FAULTS
Nadal – 2/1
Van de Zandschulp – 3/3

BREAK POINTS WON
Nadal – 6/12
Van de Zandschulp – 2/3

Holger Rune won his first ever ATP tour title on Sunday, but admitted it was the "worst way to win a final" after opponent Botic van de Zandschulp retired in the BMW Open final.

Both men were playing in their maiden tour-level final on debut at the ATP 250 event in Munich, and Rune becomes the third-youngest Munich champion in the Open Era.

Eighth-seed Van de Zandschulp was leading 4-3 in the first set, with his Danish opponent serving at 40-15 when the Dutchman retired due to an aching chest.

"This was probably the worst way to win a final,” Rune said. "I was obviously expecting a very tough match and he came out very strong.

"I just wish him all the best, a speedy recovery, and we all just hope to see him back on the court very soon."

Rune, who turned 19 on Friday, had a memorable week in Germany, including securing his first victory against a top 10 opponent when he beat world number three Alexander Zverev in the second round, before also getting past Jiri Lehecka, Emil Ruusuvuori and Oscar Otte on his way to the final.

"I'm super happy, of course," Rune continued. "As I said, not the way I want it to end, but if I look through the week, what a week.

"I played some unbelievable tennis, really fighting my way through it. To be playing here in Munich and winning my first ATP title in front of such a brilliant crowd, I couldn't really ask for more."

Frances Tiafoe downed fellow American Sebastian Korda in a hard-fought encounter to reach the final of the Estoril Open, while Holger Rune reached a first title match at the BMW Open.

Korda had eliminated top seed Felix Auger-Aliassime in the quarter-finals in Portugal to set up an all-American last-four clash, and looked on course to reach the final after winning the first set against Tiafoe.

However, the fifth seed roared back to seal a 4-6 7-6 (7-2) 6-4 victory and set up a final encounter with Argentina's Sebastian Baez, who beat Albert Ramos-Vinolas to reach his second tour-level final.

Baez also needed three sets in his semi-final clash after losing a competitive second-set tie-break, but he then produced a scintillating performance to win the decider without dropping a game, winning 6-3 6-7 (7-9) 6-0.

Elsewhere, Danish 19-year-old Rune sealed his first ATP tour final appearance by beating home favourite Oscar Otte 6-4 6-4 at the BMW Open in Munich.

Rune, who has enjoyed a dream week in Bavaria after sensationally downing Alexander Zverev in the last-16 and failing to drop a single set in the tournament, revealed his ambitions to become world number one in the future after the victory.

"It's a pretty unreal feeling," he said of his semi-final win. "I didn't expect this at all coming into this tournament, and I just took it match by match. Obviously, I had a tough draw, playing Zverev in the second round, but I knew it was going to be tough, so I was ready from the beginning, and I'm super happy to be in the final.

"It's getting better and better, I'm improving every day, and this is what matters. I have some goals to be number one in the world, and you have to start somewhere."

Rune will face eighth seed Botic van de Zandschulp in the final after the Dutchman rallied to beat Miomir Kecmanovic 2-6 7-6 (7-4) 6-4 in his own final-four encounter. 

Top seed Felix Auger-Aliassime fell to Sebastian Korda in the Estoril Open quarter-finals, while Casper Ruud was sent packing at the BMW Open. 

Auger-Aliassime won just 50 per cent of points behind his first serve as Korda claimed an impressive 6-2 6-2 success over the Canadian in one hour and 29 minutes. 

In the semi-finals Korda will take on fellow American Frances Tiafoe, who edged out Alejandro Davidovich Fokina 7-6 (7-5) 5-7 7-5 in a tight encounter. 

The other last-four clash will see Albert Ramos Vinolas take on Sebastian Baez. 

Ramos Vinolas bested Fernando Verdasco 6-2 6-2 to set up his meeting with Baez after the Argentine rallied from a set down to defeat Richard Gasquet 3-6 6-1 6-4. 

At the BMW Open, second seed Ruud fell to Botic van de Zandschulp in the quarter-finals. 

The Dutchman won their only previous encounter en route to the last eight at last year's US Open and he triumphed 7-5 6-1 in Munich. 

"Maybe the score is easier than it really was," said Van de Zandschulp. "The first set [was] really tight, I think. A great battle in the first one. I had some opportunities to break him in the beginning and didn't take them. Gladly [at] five-all I made the break and held the serve at 6-5. 

"[The] second set was a little bit easier, but I think I played really well today." 

Next up for Van de Zandschulp is Miomir Kecmanovic, who defeated Nikoloz Basilashvili 7-6 (7-5) 6-2. Holger Rune will continue his impressive run against Oscar Otte in the other semi-final after they overcame Emil Ruusuvuori and Alejandro Tabilo respectively.