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.
Centre Court rises for one of its favourite champions 👏
— Wimbledon (@Wimbledon) July 7, 2023
Thank you for another classic match, @andy_murray.#Wimbledon pic.twitter.com/2SMMxz1hmg
Tsitsipas said: “It’s never easy against Andy. It was a very difficult game, I’m very impressed the way he holds up having been so many years on the tour, having had two hip surgeries. I was very impressed with his level and I wish him the best.
“It was nerve-racing. I had to overcome it. It’s difficult when you’ve grown up watching him play on this court. I looked up to him, I looked up to him, Novak, Roger and Rafa. These four guys shaped the game and they’re the reason I’m the player I am today.
“I had to work extra hard today to get that victory. My legs are sore right now. He made me run left and right, up and down.”
British number one Cameron Norrie lost his second-round match at Wimbledon to American world number 43 Chris Eubanks.
Norrie, a semi-finalist last year, went down 6-3 3-6 6-2 7-6 (3) on Court One.
World number one Carlos Alcaraz had to work hard on his second Centre Court appearance to earn a straight-sets victory over Alexandre Muller in round two.
Alcaraz was given a stern examination by France’s Muller during a contest that lasted two hours and 32 minutes, but ultimately progressed 6-4 7-6 (2) 6-3.
It made it seven consecutive wins on grass for the top seed, who is viewed by many as the most likely candidate to stop defending champion Novak Djokovic in his pursuit of a record-equalling eighth title at the All England Club.