Defending champion and world number one Carlos Alcaraz stands in the way of British success at the US Open, which starts in New York next week.
Three of the four British men who have qualified automatically have been drawn in the same quarter as the Spaniard, who also claimed his first Wimbledon title over Novak Djokovic in July.
Alcaraz, who starts against Germany’s Dominik Koepfer, is seeded to face Dan Evans in round two and Cameron Norrie in round three.
Meanwhile he could also face Andy Murray in the last eight if Murray, the 2012 champion, battles through a tough draw that could include Grigor Dimitrov in round two and sixth seed Jannik Sinner in round four.
Jack Draper, the only British player not drawn in the same quarter as the irrepressible Spaniard, starts against Romania’s Radu Albot.
The draw also raises the prospect of Alcaraz renewing his quarter-final rivalry with Sinner, one year on from their epic last eight clash that lasted more than five hours and ended shortly before 3am.
Reigning women’s champion Iga Swiatek starts against Sweden’s Rebecca Peterson and could face a quarter-final meeting with sixth seed Coco Gauff.
Gauff – who is likely to have to negotiate surging 16-year-old Mirra Andreeva in round two – beat Switek for the first time in eight attempts in Cincinnati last week.
Caroline Wozniacki will face a qualifier as she makes her return after a three-year retirement and could meet former Wimbledon champion Petra Kvitova in round two.
British number one Katie Boulter starts against Diane Parry of France, and could meet another French player, seventh seed Caroline Garcia, in round two.
Boulter lost in the first round of her only previous main draw appearance in 2021, but is enjoying a fine season including a run to the third round of Wimbledon.
Jodie Burrage will make her US Open draw debut against Anna Blinkova, with a second round meeting with second seed Aryna Sabalenka the likely prize.
Osaka sees encouraging Italian Open run halted by Zheng in last 16
Naomi Osaka's promising Italian Open run was halted by Zheng Qinwen on Monday, as the seventh seed denied the four-time grand slam champion a quarter-final place.
Following Saturday's triumph over Daria Kasatkina – her second successive straight-sets win over a top-20 opponent in Rome – Osaka laughed off the "Clayomi" moniker given to her by some fans.
On Monday, her old troubles on the surface came back to the fore as Zheng dominated from the off to make the tournament's last eight for a second straight year, winning 6-2 6-4.
Osaka saw her serve broken in the very first game only to hit straight back, but Zheng assumed control by taking seven straight games to go from 2-1 down in the opener to 2-0 up in the second set.
The 21-year-old produced a clinical performance and converted all four of her break points, winning 78 per cent of first-serve points to Osaka's 68 per cent as she teed up a quarter-final clash with either Coco Gauff or Paula Badosa.
Data Debrief: 'Clayomi' no more as Zheng triumphs
Osaka impressed on a surface long regarded as her worst in Italy, but it was a bridge too far for her on Monday, Zheng reaching her fourth WTA 1000 quarter-final.
Since the format's introduction in 2009, she is just the second Asian player to reach multiple quarter-finals on both hardcourts and clay at that level before the age of 23, the other being Osaka.
Djokovic bemoans 'completely off' performance after early Italian Open exit
Novak Djokovic lamented his dismal showing as Alejandro Tabilo profited from the world number one's "completely off" performance to triumph at the Italian Open.
Tabilo stunned Djokovic with a straight-sets victory in the third round on Sunday, winning 6-2, 6-3 in his maiden ATP Tour clash with the Serbian.
The Chilean advances to the fourth round at a Masters 1000 event for just the second time after Indian Wells in 2023, with Djokovic unable to explain his struggles in Rome.
"I just wasn't able to find any kind of good feelings on the court, to be honest, striking the ball. I was completely off," he said.
A six-time champion in Rome, the 36-year-old won his opening-round match at the ATP Masters 1000 event against Corentin Moutet.
However, Djokovic was inadvertently hit on the head by a falling water bottle when leaving the court after that victory.
Whether that incident impacted his performance against Tabilo remains to be seen.
"I don't know, to be honest. I have to check that," he said. "Training was different. I was going for [a] kind of easy training yesterday.
"I didn't feel anything, but I also didn't feel the same. Today under high stress, it was quite bad – not in terms of pain, but in terms of this balance.
"Just no coordination. Completely different player from what it was two nights ago. Could be. I don't know. I have to do medical checkups and see what's going on."
Tabilo's next opponent will be Karen Khachanov, who saw off Francisco Cerundolo 6-2, 6-4, while Djokovic is made to wait for his 1100th match win.
Djokovic stunned in straight-sets defeat at Italian Open
Novak Djokovic is out of the Italian Open after a straight-sets defeat by Alejandro Tabilo in the third round on Sunday.
Tabilo recorded the biggest win of his career with a dominant performance, winning 6-2, 6-3 in his maiden ATP Tour clash with the Serbian.
Djokovic, who was hit on the head by a water bottle following his second-round win over Corentin Moutet, struggled to get going as he saw his serve broken four times.
Tabilo clinched the opening set in style, making few errors, and Djokovic failed to mount a comeback in the second, with double faults costing him at key moments, including one on the final break serve.
The Chilean advances to the fourth round at a Masters 1000 event for just the second time after Indian Wells in 2023. His next opponent will be Karen Khachanov, who saw off Francisco Cerundolo 6-2, 6-4.
Data Debrief: Big winner
Tabilo is the second player from Chile to defeat the World No.1 in ATP-1000 events after Fernando Gonzalez, who defeated Lleyton Hewitt at the Hamburg Masters in 2003, since the introduction of the format in 1990.
He is also the first Chilean to defeat a World No. 1 since Fernando Gonzalez beat Roger Federer at the 2007 Nitto ATP Finals Round Robin.
Djokovic, meanwhile, is made to wait for his 1100th match win.
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