Heartbreak for Dimitrov as he retires when two sets up on world number one
The 34-year-old Bulgarian was two sets up and playing some inspired tennis when, at 2-2 in the third set, he clutched his chest after serving an ace.
Sinner rushed around the net to check on his opponent as he sat, in some distress, on the court.
The 19th seed was helped to his feet by two physios and went off to receive treatment, before returning a few minutes later to shake Sinner's hand.
It was more dreadful luck for a popular player, who had to retire injured from matches in the last four grand slams, including against Daniil Medvedev here at the same stage last year.
Sinner, who helped Dimitrov pack his rackets away and carried his bag off court, said: 'I don't know what to say. He is an incredible player, I think we all saw this today.
'He's been so unlucky in the past couple of years. An incredible player, a good friend also. Seeing him in this position, if there would be a chance he could play the next round he would deserve it.
'I hope he has a speedy recovery. I don't take this as a win at all. This is just a very unfortunate moment to witness for all of us.
'In the last grand slams he struggled a lot. Seeing him again having this kind of injury is very, very tough. It's very sad. We all wish him only the best, let's have applause for him.'
It was a major reprieve for Sinner, the three-time grand slam winner who looked set to be on the end of a seismic shock in front of a stunned Centre Court.
The Italian had slipped on the baseline in the opening game and took a medical timeout midway through the second set for treatment on his right wrist and elbow.
But the physio was unable to alleviate the real pain for Sinner, which was Dimitrov serving up a grass-court clinic on a surface the 23-year-old has yet to get to grips with.
However, after two hours and eight minutes of vintage Dimitrov, his body let him down again, so it is the top seed who will face American Ben Shelton in the quarter-finals.
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