Andrey Rublev suffered a first-round defeat to Alex de Minaur on a bad day for the big names at the Rotterdam Open.
Second seed Rublev won this event two years ago but there will be no such run this time around after his 6-4 6-4 loss on Wednesday.
De Minaur broke the world number five early in each set and sealed the win at the first time of asking, moving to a 3-0 head-to-head record against Rublev on hard courts.
The Australian will face Maxime Cressy in the next round, who bounced back from his Open Sud de France final defeat by beating Tim van Rijthoven.
Jannik Sinner saw off Cressy in that Montpellier showdown and the Italian carried that form into this tournament, though he needed three sets to overcome Benjamin Bonzi.
Frenchman Bonzi forced a decider but Sinner regained his composure in the final set to prevail 6-2 3-6 6-1 and set up a heavyweight clash with top seed Stefanos Tsitsipas.
There was no such progress for Alexander Zverev, who joined Rublev in suffering an early exit.
The German came unstuck 4-6 6-3 6-4 to home favourite Tallon Griekspoor, whose four wins over top-20 opponents have all come in Rotterdam.
Stan Wawrinka, the champion in 2015 and runner-up four years later, will face the winner of that tie, after he beat Richard Gasquet 6-3 6-3 to reach the quarter-finals.
Holger Rune reached the semi-finals in Montpellier, and like Sinner the fourth seed progressed into round two, claiming a routine straight-sets victory over qualifier Constant Lestienne.
"It was tricky. It's a lot about finding the rhythm here in the beginning of the tournament and first match you have to really be on your toes, especially I played a qualifier today who already has two matches in his bag," Rune said.
"It made it more difficult, but I'm happy how I handled every situation today."
Hubert Hurkacz was another seed to fall out, with the world number 10 going down 7-6 (7-4) 7-6 (7-5) to Grigor Dimitrov.
Djokovic thrilled by prospect of 'one last dance' with Nadal
Novak Djokovic is thrilled by the prospect of meeting Rafael Nadal for "one last dance" at the Paris Olympics, if the Spaniard overcomes an injury setback to feature at Roland-Garros.
Thursday's men's singles draw saw Djokovic paired with Australia's Matthew Ebden in the first round, with Nadal taking on Marton Fucsovics.
The legendary duo – who have won 46 grand slam singles titles between them – will meet in the second round if they both advance through their openers this weekend.
Djokovic and Nadal have previously faced off on 59 occasions, with the Serbian winning 30 of those contests but losing four of the last six, the most recent being a Nadal victory in four sets in the 2022 French Open quarter-finals.
Nadal's participation at the Games was thrown into doubt when his coach Carlos Moya said he had suffered a "setback" on Thursday and required 48 hours of rest.
If Nadal – who is widely expected to retire later this year – does make the tournament, Djokovic is looking forward to the prospect of facing him for a 60th time.
"Obviously he hasn't played much. His ranking dropped, so there was always going to be that possibility of me meeting him in an early round and there we go," Djokovic said.
"It's going to be a spectacle, definitely, if we get to meet. We will spread some fireworks on the court, like the good old times.
"I hope we get to meet because it will probably be one last dance for the both of us."
Djokovic is set to appear at his fifth Olympics in the French capital, the joint-most by any male player since the sport returned to the Games in 1988 (with Yen Hsun Lu).
He is the player with the most matches played (19) and joint-most matches won (13, level with Roger Federer) at the Olympics since 1988.
However, his best result at the Games remains a Bronze medal at Beijing 2008, when he was beaten by eventual gold medallist Nadal in the semi-finals.
Djokovic lost the bronze medal match to Pablo Carreno Busta at the delayed Tokyo Games three years ago, also losing to Juan Martin del Potro at both London 2012 and Rio 2016.
Linette dominates first all-Polish WTA final to win Prague Open
Magda Linette rounded off her Olympic preparations in style as she claimed her third WTA title with a comfortable win over Magdalena Frech at the Prague Open.
Linette, who beat Viktoriya Tomova and Linda Noskova on her way to the final, won in straight sets 6-2 6-1 as she now heads to Paris to face Mirra Andreeva.
The world number 41 was in the ascendency from the off, forcing a break in the fourth game and never looking back.
Despite the best efforts of Frech, who saved one set point, Linette continued to apply the pressure and another break put her a set up.
Linette would again break in the fourth game of the second set, winning three games on the bounce to secure her first career win over her compatriot.
Data Debrief: Linette prevails in first all-Polish affair
The final in Prague between Linette and Frech was the first all-Polish WTA level final in the Open Era.
Linette's triumph over her opponent was her first, having lost in the pair's previous encounter in Saint-Malo back in 2022.
During the contest, the world number 41 gave nothing away, saving all four of the break points she faced while converting three of the seven she had against Frech.
Nadal suffers injury 'setback' as Olympics participation thrown into doubt
Rafael Nadal may be facing another injury setback at the Paris Olympic Games after his coach warned over the Spaniard's fitness.
The 22-time major champion is widely expected to retire at the end of this year, though is preparing for a final swansong at Roland-Garros, where he has won 14 titles.
Nadal is set to play in the singles and doubles tournaments of the Olympics, partnering current French Open and Wimbledon champion Carlos Alcaraz for the latter competition.
Yet his participation has become doubtful after coach Carlos Moya confirmed Nadal had cancelled his training session on Thursday due to a hamstring issue.
"It was a setback and we decided that today Rafa would rest and not train to recover," Moya said, as quoted by Spanish journalist Rafael Plaza.
"We are going to give ourselves 48 hours, we have to wait."
The 38-year-old is reportedly feeling soreness in both his left and right hamstring having pulled out of a scheduled practice session with Alexander Zverev.
Alcaraz had been partnering Nadal throughout the week during training on the clay courts of Paris, though the veteran's feature has now been thrown under a cloud of doubt.
Nadal is one of just two players to have won Olympic gold in both singles and doubles since the sport returned to the Games in 1988, doing so at Beijing 2008 (singles) and Rio 2016 (doubles).
In the singles in the French capital, Nadal has been drawn against Hungary's Marton Fucsovics in the opening round, and the prize could be a second-round date with long-term rival Novak Djokovic.
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