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.
Griekspoor heroics send the Netherlands to historic Davis Cup final
Tallon Griekspoor produced a thrilling comeback to help the Netherlands reach the Davis Cup final for the very first time after they downed Germany 2-0 in Malaga.
After losing the opening set to Jan-Lennard Struff, Griekspoor held his nerve to emerge a 4-6 (4-7) 7-5 6-4 victor on an enthralling day of action on Friday.
Earlier in the day, Botic van de Zandschulp, who beat Rafael Nadal in the final match of the Spaniard's career on Tuesday, put the Dutch 1-0 up with a win over Daniel Altmaier.
The world number 80 needed 10 match points to wrap up a tense 6-4 6-7 (12-14) 6-3 victory, after Altmaier saved five break points in a second set tie-break.
Griekspoor then stopped the best-of-three tie from going to the deciding doubles, rallying back with a fine display, though Struff let two crucial break points slip in the eighth game of the second set.
“We have been talking about this [moment] for two or three years,” said Griekspoor.
“We came here all the time with unbelievably tough draws, but we believed in ourselves so much. We always felt like this was possible.
"To do it now feels unbelievable. I am so happy for the team, and for Holland.
“I just tried to focus on my own game. I felt like he was playing unbelievable tennis, I didn’t do much wrong in the first set.
"I’m super proud of myself, super proud of the effort and very happy to get the win in the end.”
The Netherlands await either reigning Davis Cup champions Italy or Australia, who face off in the other semi-final on Saturday.
Data Debrief: Dutch delight
After reaching the semi-final stage for only the second time this century, the Netherlands produced arguably their finest display of the tournament against Germany.
It meant that after 185 ties played at the event across a 104-year timeframe, they had finally reached the showpiece match at the tournament for the first time.
But their victory was made possible by Griekspoor, who converted both his break points, while fittingly sealing his encounter with his 25th ace of the contest.
Sinner inspires comeback to help Italy reach Davis Cup semi-finals
Jannik Sinner kept Italy's hopes of retaining the Davis Cup alive after winning matches in the singles and doubles to inspire a 2-1 comeback triumph over Argentina on Thursday.
Sinner and Matteo Berrettini edged Maximo Gonzalez and Andres Molteni 6-4 7-5 in the deciding game to set up a rematch of last year's showpiece against Australia in the final four.
However, the Italians started off on the back foot when Francisco Cerundolo downed Olympic bronze medallist Lorenzo Musetti 6-4 6-1 in an hour and 29 minutes.
Musetti converted just two of the eight break points he was presented with, as Cerundolo put Argentina on the brink of reaching the semi-finals for the first time since 2016.
But two-time grand slam champion Sinner, who won the ATP Finals last weekend, carried his momentum forward from Turin against Sebastian Baez.
The world number one breezed to a 6-2 6-1 win over his opponent, serving seven aces to the Argentine's one, while also saving all four break points he faced.
Sinner then returned to the court alongside Berrettini, with the pair replacing Simone Bolelli and Andrea Vavassori in the must-win clash.
The pair won 90% of their first-serve points and fended off all five break points they faced, earning a key break at 5-5 in the second set before surging to victory.
"It was a must-win match," said Sinner. "Very different conditions. The court is very, very fast and tough to play.
"I haven't had so much time to adapt to the conditions, but I'm happy about today."
Data Debrief: The Italian Job
Italy edged closer to becoming only the sixth nation to retain the Davis Cup since the final stage was introduced 52 years ago, and first since the Czech Republic in 2013.
But they were inspired by Sinner once again, who proved why he will end the year at the summit of the ATP rankings.
And after leading Italy to their first Davis Cup title since 1976 with a victory against Australia's Alex de Minaur last year, he will fancy his chances this time around.
Ebden and Thompson send Australia to third straight Davis Cup semi
Matthew Ebden and Jordan Thompson booked Australia's place in the Davis Cup semi-finals after the pair clinched their deciding match against the United States to win 2-1.
The pair, who won gold at the Paris Olympics, beat Tommy Paul and Ben Shelton 6-4 6-4 to put Lleyton Hewitt's side into their third successive semi-final at the men's team event.
Australia, who have won the tournament 28 times, largely had Thanasi Kokkinakis to thank after his remarkable triumph over Shelton in the first match of the day.
Kokkinakis saved four match points and let slip six of his own before eventually prevailing 6-1 4-6 7-6 (16-14) in an engrossing encounter that lasted two hours and 14 minutes.
However, in the rematch of a recent ATP Finals group-stage match, Taylor Fritz emerged victorious over Alex De Minaur as he did in Turin a week ago.
Despite De Minaur going 2-0 up in the second set, Fritz roared back to earn a 6-3 6-4 victory to send the tie the distance in Malaga.
But Australia held their nerve, and will discover their opponents later on Thursday when reigning champions Italy take on Argentina.
Ebden and Thompson’s win came after United States’ captain Bob Bryan opted for a late change, with Paul and Shelton replacing Austin Krajicek and Rajeev Ram.
“We were expecting the other pair, but we knew they’ve got incredible players who can play doubles,” said Ebden.
“We were ready. A slight adjustment obviously. More huge serving singles players than the doubles craft, maybe, but it was just as big a challenge as any.
"Out here, finals live match, just to play with Jordan here was real fun. Following what Kokk did, unfortunately Alex went down, but what a day. So fun, so happy.”
Data Debrief: Australia ready to right Davis Cup wrongs
Australia have failed to win the Davis Cup since 2003, but they will be confident of halting that streak this time around.
If they take the trophy, they will have reason to thank Kokkinakis, whose tie-break win against Shelton was the longest an Australian player had featured in at the tournament, surpassing Pat Rafter's win over David Rikl in the 1997 quarter-finals of the competition (15-13).
Ebden and Thompson also shone when it mattered most, serving four aces compared to Paul and Shelton's two, while also winning 92% of their first-serve points.
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