World No 1 Jannik Sinner saw his hopes of a maiden Wimbledon title ended by Daniil Medvedev in the quarter-finals, with Carlos Alcaraz fighting back to beat Tommy Paul.
Medvedev and Alcaraz will now face one another in the men’s singles semi-finals on Friday.
Medvedev overcame a struggling Sinner to dump the top seed out of the tournament and reach a second-consecutive semi-final.
The fifth seed, who has now matched his best Wimbledon run from last year, said: “I knew if I want to beat Jannik, it needed to be a tough match. I felt at one moment he was not feeling that good but I knew it could still get away. It was great points, great match, and I’m really happy.”
Sinner appeared to be feeling unwell, holding his head in his hands after calling the doctor early in the third set, and being helped off court for a medical time-out.
A possible retirement looked on the cards but Sinner gradually improved on the resumption and may have won the match had he taken one of two set points in the third.
He managed to forced a deciding set but it was Medvedev who eventually claimed a 6-7 (9-7) 6-4 7-6 (7-4) 2-6 6-3 victory after exactly four hours to set up a clash with defending champion Alcaraz.
It snapped Medvedev’s five-match losing sequence to Sinner and avenged his bitter defeat by the Italian in this year’s Australian Open final, when he squandered a two-set lead.
The Centre Court roof magnified the crispness of the ball striking as the two men went toe-to-toe in an opening set full of long rallies, dragging each other from one corner to the other.
Neither player even threatened a break and nerves were on show in the tie-break. Both men double-faulted, Sinner at 5-5, but Medvedev missed two routine forehands and then double-faulted again on the Italian’s second opportunity.
The first signs that all was not well with Sinner came in the third game of the second set when Medvedev took advantage of lacklustre play from the top seed to break for the first time.
Sinner withstood more break points at 2-4 but, when he dropped serve again at 1-1 in the third, it was clear the 22-year-old was in trouble.
It appeared he may not be able to continue at all when he was led off court by the doctor but he walked gingerly back several minutes later and resumed.
The Italian still did not look at all well, walking very slowly between points, and he set about trying to shorten the points, mixing win-or-bust groundstrokes with drop shots.
It was enough to keep him in touch until Medvedev served for the third set, where the assurance the fifth seed had shown suddenly deserted him and from nowhere Sinner broke back.
The resurgent Italian, who was wrapping an ice towel around his neck between games, then had two chances to clinch the set but Medvedev saved one with an ace before Sinner’s backhand struck the net.
Another ace gave Medvedev the tie-break to put him a big step closer to the semi-finals only for Sinner to come surging back in a quick fourth set and send the contest to a decider.
Sinner now seemed the favourite but the momentum switched once again in the fourth game when, having saved two break points, Sinner netted a forehand.
And Medvedev was nerveless serving out his best victory at Wimbledon to reach a ninth Grand Slam semi-final.
Alcaraz books Medvedev semi-final with comeback victory vs Paul
Meanwhile, defending champion Alcaraz came from a set down to beat Paul 5-7 6-4 6-2 6-2 on Court 1 and book his semi-final place against Medvedev.
Defending champion Carlos Alcaraz will face Medvedev in the Wimbledon semi-finals, after overcoming the USA’s Tommy Paul
In an extraordinary opening set, lasting over 70 minutes, American Paul surprised Alcaraz by claiming it 7-5 after a long rally and stunning backhand shot down the line, right before a potential tie-break.
Alcaraz was then broken in his first service game of the second set, falling 2-0 down. The Spaniard showed his mettle to reply by breaking Paul just when he needed to most, holding his next service game too for 2-2.
Paul clinched an extremely long opening set win vs Alcaraz on Court 1
At 3-3, Alcaraz struck to break Paul again, going on to serve out the set with comfort at 6-4.
Into the third set, a blistering forehand drive saw Alcaraz break his 27-year-old opponent in the first game. Yet, Paul responded straightaway to break back immediately for 1-1.
A third break in succession followed as a pumped-up Alcaraz edged to 2-1, holding his next service game to move 3-1 ahead.
A rushed forehand saw Alcaraz pass up the chance of another break, while at 3-2 back on the Alcaraz serve came a determined challenge from Paul, who fought from 40-15 down to take things to deuce, but then passed up two break-point chances as the game was restored to deuce four times. In the end, it was Alcaraz who secured a vital hold, letting out a huge cry of “Vamos!”
Alcaraz played some mesmerising shots in the comeback victory vs Paul
As is the champion way, Alcaraz then backed up a tough and tight hold with an immediate break of Paul via a stunning backhand strike down the line, taking total control at 5-2 moments after the game was almost levelled, duly serving out for a 6-2 success.
Into the fourth set, Alcaraz struck for another break of Paul despite seeing 15-40 pegged back to deuce: sealing the game as Paul shot very narrowly wide.
An immense sequence of two Alcaraz rocket-forehand strikes saw him consolidate with a hold to 30, while Paul thought he had denied Alcaraz a further break in the next game with a smash volley to take things to deuce, only for the Spaniard to come back with a stunning backhand winner to go 4-1 up.
A straightforward hold followed, and the next time the 21-year-old was serving it was for the match, holding to love in another fabulously-entertaining performance.
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