Rafael Nadal missed three match points and needed medical treatment as his comeback tournament ended in a quarter-final defeat by Jordan Thompson.
Nadal looked poised to claim another straight-sets win at the Brisbane International when he brought up a first match point in the 10th game of the second set but missed a backhand overhead.
Two more chances followed in the tie-break but Nadal was unable to take either and Australian Thompson fought back to claim a 5-7 7-6 (6) 6-3 victory after three hours and 25 minutes.
More concerning was the off-court medical time-out Nadal took at 1-4 in the deciding set for treatment to his upper left leg, although he was able to continue without too much apparent discomfort.
The 37-year-old had surgery on the psoas tendon in his left hip in June after being sidelined since suffering an injury at last January’s Australian Open.
Thompson will take on second seed Grigor Dimitrov in the semi-finals, while top seed Holger Rune faces Russian Roman Safiullin.
In the women’s event, top seed Aryna Sabalenka continued to look sharp in a 6-1 6-4 victory over Daria Kasatkina, her 14th-straight win in Australia, while second seed Elena Rybakina was a set up on Anastasia Potapova when the Russian retired.
Sabalenka will take on fellow Belarusian Victoria Azarenka in the last four after she battled past Jelena Ostapenko, while Czech Linda Noskova won the battle of the teenagers against 16-year-old Mirra Andreeva.
At the ASB Classic in Auckland, defending champion Coco Gauff and second seed Elina Svitolina both eased into the semi-finals, while Alexander Zverev defeated Stefanos Tsitsipas to help Germany defeat Greece in the United Cup quarter-finals.
Meanwhile, Harriet Dart reached the biggest final of her career at the WTA 125 event in Canberra, battling to a 7-5 3-6 7-5 victory over American Katie Volynets, and Heather Watson is through to the doubles final in Brisbane with Belgian Greet Minnen.
Osaka makes winning return at Italian Open
Naomi Osaka claimed a straight sets victory over Clara Burel in the first round of the Italian Open.
Making her first appearance in Rome since 2021, former world number one Osaka prevailed 7-6 (7-2) 6-1 on Wednesday, marking her first win over a top-50 opponent on clay since she defeated Victoria Azarenka at Roland Garros in 2019.
Osaka, who is now ranked 173rd in the world by the WTA, will face Marta Kostyuk in the second round.
She previously faced Kostyuk in the 2020 US Open, en route to winning her third major title.
Data Debrief: Back with a bang
Osaka reached the quarter-finals of the Italian Open in 2019, but did not win a game in 2021 and has not appeared at any other edition since then.
That means the 26-year-old won her first match at the event since she beat Mihaela Buzarnescu in 2019 (1,819 days ago). She wrapped up the win in one hour and 24 minutes, finishing with 27 winners, including eight aces.
Winning Olympic medal 'equal to Grand Slams', says Gauff
Coco Gauff believes winning a medal at the forthcoming Paris Olympics would be "equal" to winning a Grand Slam.
The world number three was forced to miss the Games in Tokyo three years ago after testing positive for COVID-19, and is eager to sample the "once-in-a-lifetime experience".
The tennis events will be played on the clay of Roland Garros, where Gauff will be bidding for a second major title at the French Open later this month.
And the reigning US Open champion is looking forward to competing, though she admits her preparations will be unprecedented.
"For me, the Olympics is a top priority. I'd say equal to the Grand Slams," Gauff told reporters at the Italian Open, where she will face Magdalena Frech in the last 64.
"I wouldn't put it above or below just because I've never played before. This is my first time. Obviously, I always want to do well, try to get a medal. But the preparation is going to be interesting, because I've never done the grass to clay transition before.
"I'm not putting too much pressure on it because I really want to fully indulge in the experience. Hopefully, I can have it many times in my lifetime. I'll treat it as a once-in-a-lifetime experience."
Before that, Gauff is focused on getting ready for the French Open, where she was runner-up to world number one Iga Swiatek two years ago.
The 20-year-old will step up her preparation at the Italian Open this week, aiming to build on her run to the round of 16 at the Madrid Open last time out, where her run was ended by compatriot Madison Keys.
"For me, it's just about serving better than I did last week," she added. "I feel the other parts of my game are improving. If I can work that through, I think it'll set me up for a very good Roland Garros."
Madrid champion Swiatek keen to maintain level at Italian Open
Iga Swiatek will not rest on her laurels after overcoming Aryna Sabalenka in last week's Madrid Open final, pledging to learn from that gruelling battle ahead of the Italian Open.
Swiatek toppled Sabalenka in an enthralling battle between the world's top two players on Saturday, saving three championship points en route to a 7-5 4-6 7-6 (9-7) win in over three hours on court.
The world number one has now won every European clay court tournament at WTA 500 level or higher, including back-to-back triumphs in Rome in 2021 and 2022.
As she prepares to open her Italian Open campaign against either Caroline Dolehide or a qualifier on Friday, Swiatek is determined to ensure she does not let her level drop.
Speaking during an appearance on the WTA Insider Podcast, Swiatek said: "I feel like after such a match, I deserve a two-month vacation, but I can't have that so I'll trade it for six tiramisus or something!
"I can let it go and rest and just forget about it, or I can really take a big lesson from it, so it depends on what is going to happen in the next few weeks in terms of how I analyse it."
Swiatek's latest win – her seventh in 10 meetings with Sabalenka – saw her put further distance between herself and the world number two in the WTA rankings.
However, the four-time grand slam champion knows she cannot afford to let up, given the fierce competition on the WTA tour.
"I'm not thinking about Aryna when I'm practising, but it's more that I know that the competition is big and if I stop for a while I might be pushed out," Swiatek said.
"But I had this kind of thing in Rome 2022, with the final against Ons [Jabeur]. Physically, I was so tired. The rallies were long, Ons was playing a pretty tricky game.
"So after that game for the next few years, when I was doing the worst practices on court and I was dying, I was thinking about that game."
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