Rafael Nadal joined Daniil Medvedev in making a shock early exit from the Paris Masters on Wednesday.
While world number one Carlos Alcaraz overcame Yoshihito Nishioka 6-4 6-4 to progress to the last 16, there was no such luck for compatriot Nadal, whose chances of ending the year at the top of the ATP rankings are over after a defeat to Tommy Paul.
World number two Nadal looked well set to progress after claiming the first set 6-3 in just over 40 minutes, yet American Paul rallied to seal the biggest win of his career 3-6 7-6 (7-4) 6-1.
The 22-time grand slam champion said on Tuesday that he is no longer concerned with competing for the top spot in the world, though he will no doubt be frustrated at bowing out at the first hurdle ahead of the ATP Finals later this month.
Paul became the first player to defeat Nadal prior to the quarter-finals of the tournament when he sent a controlled backhand volley away from the forlorn 36-year-old.
Nadal was not the only big-name exit, with world number three Medvedev also slumping to defeat, going down 6-4 2-6 7-5 to Alex de Minaur.
For Australian De Minaur, it was his first win in 19 attempts against a player ranked in the top five and sets up a third-round clash with Frances Tiafoe, who beat Jack Draper.
"It's a good one to get, for sure," said De Minaur. "It's the end of the year, everyone's a bit tired, but I'm very proud of my performance. I just played very smart.
"I knew it was going to be a chess match out there, both baiting each other to be aggressive, but you also didn't want to be too aggressive at times. It was an absolute battle and I'm very happy I was able to come out on top."
It leaves the path open for Alcaraz to retain his place as the world's best player, and the 19-year-old said after his win: "First round in every tournament is never easy.
"You have to be really focused, you have to try to get a good rhythm, good feeling in the first round. I'm really happy with the performance, the level that I played, and I'm looking forward to getting better in the next round."
Ninth seed Taylor Fritz and 10th seed Hubert Hurkacz lost to Gilles Simon and Holger Rune respectively, their defeats ensuring Felix Auger-Aliassime, who overcame Mikael Ymer, and Andrey Rublev will feature in the ATP Finals.
Auger-Aliassime's victory took three hours and 30 minutes, and marked his 14th win in a row.
"Somehow I found a second wind after saving those break points at 4-1," said the Canadian.
"I played better and better, coming through the court much better, serving better. It was pretty epic. Three hours and 30 minutes on the court, quality rallies. He was making me work all the time. Definitely a win to remember."
Fifth seed Stefanos Tsitsipas was also a winner, seeing off Daniel Evans in straight sets.
Raducanu stunned by qualifier Carle in Madrid
Maria Lourdes Carle made a splash at the Madrid Open on Wednesday, as the qualifier sent Emma Raducanu packing.
World number 82 Carle stepped into the void to fill in for Karolina Pliskova, who withdrew prior to the end of the qualifying rounds, to face 2021 US Open champion Raducanu.
It is just the second time Carle has reached the main draw of a WTA 1000 event, and she ensured it would be a memorable campaign after a 6-2 6-2 victory over Raducanu, who is now ranked at world number 221, though has enjoyed something of a return to form this season.
Raducanu reached the quarter-finals of the Stuttgart Grand Prix last week, going down to world number one Iga Swiatek, but has recently enjoyed victories over the likes of Angelique Kerber and Caroline Garcia.
Data Debrief
Carle is the first player from Argentina to defeat a former women's singles grand slam Champion since Nadia Podoroska overcame Serena Williams in Rome in 2021.
The 24-year-old is making just her sixth WTA main draw appearance, with her first WTA 1000 appearance having come in Miami in March.
'I will play Roland Garros if I feel competitive' – Nadal uncertain on French Open participation
Rafael Nadal is unsure as to whether he will be fit enough to feature at the French Open.
Nadal is embarking on a swansong season, having indicated he will retire after the 2024 campaign.
The 37-year-old is set to make his farewell appearance at the Madrid Open this week, with his campaign starting against American teenager Darwin Blanch on Thursday.
Nadal, now ranked 512 in the world, has played just five Tour-level matches this year, as he makes his comeback from yet another injury lay-off.
And the 14-time Roland Garros champion acknowledged on Wednesday that he would be unlikely to play at the French Open should it be taking place this week.
"If I was in Paris today, I wouldn't go out to play," he said.
"I don't think I'll be able to play at 100 per cent, but it's important to be able to play for the last time in Madrid.
"It means a lot to me to play on this court where I've had some great moments."
Thankfully for Nadal, the French Open does not take place until late May, giving him time to get fit.
"If I arrive in Paris the way I feel today, I will not play," he said.
"I will play Roland Garros if I feel competitive. If I can play, I play. If I can't play, I can't. It won't be the end of the world or the end of my career. I still have goals after Roland Garros, like the Olympics.
"Few weeks [ago], I didn't know if I would be able to play again on the professional tour. It's not perfect but at least I am playing and I can enjoy again, especially in the tournaments that are so emotional for me.
"I'm able to enjoy the fun that I can say, probably, goodbye on court. Without trying to confuse anyone, I don't know what's going to happen in the next three weeks.
"I'm going to do the things I have to do to be able to play in Paris. And if I can, I can and if I can't, I can't. I'm going to Paris if I feel like I'm good enough. I'm going to Paris if I feel capable enough to compete."
Nadal played three times in Brisbane in January, losing to qualifier Jordan Thompson and subsequently missing the Australian Open.
He featured twice in Barcelona earlier in April, losing to Alex De Minaur in the round of 32.
Nadal has won five titles in Madrid, though, and the tournament holds a special place for him, as he underlined his determination to compete.
He added: "Some moments I find myself enjoying being on court, playing against the best players again and I feel myself, more or less competitive, and other moments I feel limitations and it’s difficult.
"The goal is to be on court, enjoy it as long as possible. I mean, that's the thing, enjoy the fact that I will be able to compete one more time on the professional tour and here at home in Madrid, a place that gives me everything in terms of support.
"I am here giving myself a chance. If at some moment my situation improves, if I am able to find better feelings in my body, I need to be ready."
Osaka storms to victory in Madrid opener to end long wait for win on clay
Naomi Osaka comprehensively dispatched Greet Minnen on Tuesday to make a winning start to her Madrid Open campaign and earn a first win on clay for two years.
Japanese star Osaka triumphed 6-4 6-1 in only 79 minutes, swiftly booking a second-round clash against Liudmila Samsonova.
Osaka reached the last 32 at the WTA 1000 events on the hard courts of Indian Wells and Miami but had lost to Martina Trevisan at the first hurdle in the Open de Rouen on clay at WTA 250 level last week.
This was therefore a welcome return to form against Belgian qualifier Minnen and represented her first triumph on the surface since beating Anastasia Potapova at this tournament in 2022.
After an even start to the contest, the first set was level at 4-4. But Osaka then assumed full control, winning eight of nine games to race to victory.
Data Debrief: Osaka dominates on serve
Osaka was not broken at all in the match and allowed Minnen only one break-point opportunity across the whole contest.
She fired down eight aces to only three double faults, and won 13 of her 16 first-serve points in the second set.
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