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Andy Murray suffered more Wimbledon heartache with a five-set defeat by
Stefanos Tsitsipas in their delayed second-round clash, while Cameron Norrie also exited on Friday afternoon.

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 (7-3) 6-7 (2-7) 4-6 7-6 (7-3) 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.

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 [on Friday] to get that victory. My legs are sore right now. He made me run left and right, up and down.”

Andy Murray waves to the crowd after losing against Stefanos Tsitsipas (not pictured) on day five of the 2023 Wimbledon Championships at the All England Lawn Tennis and Croquet Club in Wimbledon. Picture date: Friday July 7, 2023.
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Was Murray waving goodbye to Wimbledon Centre Court for the final time?

Murray, who 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.

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 shootout, it was Tsitsipas who won the final four points in breezy conditions.

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.

Tsitsipas: The Grand Slam slayer

Stefanos Tsitsipas is the first player to defeat two former Grand Slam champions in the first and second round of a Grand Slam since Nikolay Davydenko at the French Open in 2008, and the first in Wimbledon since Dick Norman in 1995 (Pat Cash and Stefan Edberg).

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.

Cameron Norrie leaves the court after his defeat to Christopher Eubanks on day five of the 2023 Wimbledon Championships at the All England Lawn Tennis and Croquet Club in Wimbledon. Picture date: Friday July 7, 2023.
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Cameron Norrie was knocked out of Wimbledon by Christopher Eubanks

Just minutes earlier, British No 1 Cameron Norrie lost his second-round match to American world No 43 Christopher Eubanks.

Norrie was left dazed by Eubanks’ powerful hitting and his haymaker of a serve in a punishing 6-3 3-6 6-2 7-6 (7-3) defeat.

In a heavyweight start to the contest, the first 20 points all went with serve including nine aces, seven from the arm of Eubanks.

It was the world No 43 who landed the first blow, breaking Norrie to love on his way to taking the opening set.

Norrie, the 12th seed and a semi-finalist last year, had barely laid a glove on his opponent, winning just three points on the Eubanks serve.

But the South-African-born southpaw hauled himself off the canvas and secured an early break in the second set to level the match.

However, Norrie has looked ring-rusty in recent months and Eubanks, a grass-court title-winner in Mallorca in June, took advantage by breaking twice for the third set.

Eubanks dropped his guard in the fourth, losing his serve to love, but he hit back for 4-4 to leave Norrie on the ropes.

Norrie survived a match point on serve when a Eubanks forehand thudded into the net.

But Eubanks was too strong in the tie-break, a quick one-two of a booming forehand and delicate volley leaving Norrie out for the count.

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