Jannik Sinner out of Wimbledon after losing five-setter with Daniil Medvedev

Daniil Medvedev overcame a struggling Jannik Sinner to dump the world number one out of Wimbledon in the quarter-finals.

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 (7) 6-4 7-6 (4) 2-6 6-3 victory after exactly four hours.

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.”

This was a rematch of the Australian Open final, where Medvedev had led by two sets to love only for Sinner to battle back and claim his first grand slam title.

Having lost his first six matches against the Russian, Sinner went into this encounter looking to even the head-to-head.

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 man 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, as rain hammered on the roof, 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.

The top seed 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.