Andy Murray suffered more Wimbledon heartache with a five-set defeat by Stefanos Tsitsipas in their delayed second-round clash.
The Scot was two sets to one up overnight when the 11pm curfew came into play but he was unable to complete the job, with fifth seed Tsitsipas fighting back to win 7-6 (3) 6-7 (2) 4-6 7-6 (3) 6-4.
It was a hugely disappointing way for Murray to mark the 10th anniversary of his career-defining first Wimbledon title, and he is all too aware that his chances for another deep run here are ebbing away.
He missed the French Open to focus on his grass-court preparations and arrived at the All England Club feeling confident and healthy for the first time since winning his second title in 2016.
He was unfortunate to run into a top seed so early, and there were many aspects of his performance that were positive, but he would have fancied his chances against Tsitsipas on grass and this one will sting.
The match began under the roof on Thursday but there were blue skies above on the hottest day of the tournament so far when the players returned to Centre Court.
Murray had sparked alarm right at the end of the set by screaming in pain and going down clutching his left groin but he practised as normal ahead of the match and there was no sign of any discomfort.
The breezy conditions perhaps contributed to more errors from both than was the case in the first part of the match, while nerves were sure to play their part with the contest already so close to its conclusion.
Tsitsipas’ backhand leaked a substantial number of errors but his serve was again working beautifully and Murray was unable to force a break point, the 36-year-old smacking the net in frustration as another close game got away.
He had clearly been eager to avoid the lottery of another tie-break and, in a repeat of the first-set shoot-out, it was Tsitsipas who won the final four points.
Murray’s strategy to relentlessly probe the Greek’s backhand was perhaps becoming a little predictable, and he was in serious trouble when Tsitsipas created three break points in the third game of the deciding set, taking the third to break serve for the first time.
Willed on by the crowd, Murray tried to find a way back but Tsitsipas continued to serve very strongly.
Still there was hope as the home favourite saved two match points but he clinched it on his third chance with his 17th ace to book a third-round clash with Laslo Djere.
ATP Finals: Sinner happy to come through 'very tough match' against Fritz
Jannik Sinner insisted he was prepared for the "aggressive" Taylor Fritz in their first meeting since the US Open final in September at the ATP Finals on Tuesday.
Sinner improved his record over Fritz to 3-1 with a 6-4 6-4 victory in Turin, going level with Alexander Zverev with a Tour-leading 67th victory of the season.
The Italian now sits at the top of the Ilie Nastase Group after two games, and faces Daniil Medvedev on Thursday, with the Russian beating Alex de Minaur in straight sets.
"It was a very tough match. We got to know each other from a grand slam final," Sinner said.
"We knew exactly what to expect today. He was very aggressive, but I was prepared too. I just tried to serve well in the important moments.
"In the return positions, his quality of tennis was very, very high, so I was struggling to return his serve, but I was happy with the situation.
"It was a very important day for me today, and I'm very happy that I got through."
Sinner fought off tough resistance from Fritz in front of a home crowd in Turin, hitting 22 winners compared to his opponent's 19.
Fritz had initially earned the first break point of the match, but was unable to make it count before fighting back from 0-40 to level the first set at 4-4.
Sinner ultimately piled the pressure on to win the first set and capitalised on a double fault in the second to break Fritz and win. Fritz will now face de Minaur on Thursday.
ATP Finals: Sinner stays perfect with assured Fritz victory
Jannik Sinner continued his quest to end his stellar season with the ATP Finals title after downing Taylor Fritz in straight-sets to earn his second win of the tournament.
Sinner emerged a 6-4 6-4 victor in an hour and 40 minutes in Turin, with his latest triumph improving his record to 7-0 on indoor hard courts in 2024.
The Italian showed his intentions with a love service game to open the first set, but was matched by his American opponent, who was also looking to maintain his perfect start.
Sinner missed four break points in the eighth game, but made no mistake in Fritz's following service game to claim the early advantage in Turin.
Fritz again traded blows with the year-end world number one, but would again lose a decisive break late in the second set that put Sinner within touching distance.
The American exchanged in another pulsating rally with his opponent, but sent a backhand wide to send Sinner through and to the top of the Ilie Nastase Group after two matches.
Up next for Sinner is Daniil Medvedev, who beat Alex de Minaur earlier on Tuesday, while Fritz will face the Australian on Thursday.
Data Debrief: The Italian Job
In a back-and-forth tussle with Alexander Zverev to end the year with the most wins, Sinner levelled the German with his Tour-leading 67th victory in 2024 on Tuesday.
He also sealed a 12th win against an American opponent this season, only managing more wins against Ben Shelton (three) this season than Fritz (two, level with Alex Michelsen).
Sinner (2023-24) is only the third player in the Open Era to claim 47+ ATP match wins on hard court in consecutive seasons after Roger Federer (2005-06) and Novak Djokovic (2012-13, 15-16).
Daniil Medvedev credited his ability to "block out the noise" as crucial in getting his ATP Finals campaign up and running with a straight-sets victory over Alex de Minaur.
Medvedev, who lost his opening game of the tournament to Taylor Fritz, returned to winning ways with a 6-2 6-4 triumph over the Australian in 78 minutes on Tuesday.
The Russian cut a frustrated figure in his defeat to Fritz on Sunday, breaking his racket and was docked a point after serving a third consecutive double fault during the encounter.
However, the fourth seed produced an expertly measured performance, winning 20 out of 31 baseline points in the opening set to claim the early advantage.
The second set was more evenly contested, but Medvedev secured a crucial break point in the ninth game, going on to seal his first top 10 win on hard courts since March.
"After the last match I was too tired to fight mentally the way I do and so, during the match, when it doesn't work your way, you want to win and when you start losing you get frustrated," Medvedev said.
"So I went into this match thinking, if I lose I go home on Thursday for sure and if I win then I have the chance to have a good feeling. I tried to hit some shots and it worked well and I'm ok with it.
"A lot of football players do it [block the noise]. It's more about social media and for sure after my performance with Taylor and some of my comments ... I tried to read it less.
"I went into this match trying to block the noise even from myself, so no tantrums and I really didn't care what was happening on the court."
Medvedev will seek to bolster his hopes of progressing from the John Newcombe Group when he takes on Jannik Sinner next, with the Italian in action against Fritz later on Tuesday.
Data Debrief: Cool, calm and collected
Medvedev kept his hopes of sealing a second ATP Finals crown alive with a composed display against De Minaur, improving his record to 45-19 for the season.
While the Russian produced more unforced errors (18) than De Minaur (15), Medvedev showed his quality by hitting 24 winners, 14 of which came with his forehand.
Medvedev also claimed his sixth top 10 win of 2024, while also improving his head-to-head record against his Australian opponent to 7-3, avenging his defeat in the French Open round of 16 earlier this year.
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