Dimitrov won the first two sets in brilliant fashion against the world No 1, with the 6-3, 7-5 scoreline a worthy reflection of his exceptional performance.
Yet as he served at 2-1 in the second set, closing in on one of the biggest upsets of the tennis year, Dimitrov felt his pectoral before he hit an ace to take the score in the third set to 2-2.
The moment he struck that ace, he sank to the floor on Centre Court and appeared to realise instantly that all of his hard work would count for nothing.
Dimitrov went off court for treatment, but quickly returned to concede defeat, with Sinner offering plenty of sympathy for his opponent as the Bulgarian was forced to pull out of his fifth successive Grand Slam due to injury.
“I don’t know what to say. He is an incredible player and we all saw this today,” said Sinner.
“He has been so unlucky in the past couple of years. He is an incredible player who is a good friend of mine. We understand each other very well off the court.
“Seeing him in this position – if there was a chance for him to be in 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 an unfortunate moment for us to witness.
“He has struggled in Grand Slams with injuries a lot so seeing him again with this injury is very tough. We all saw by his reaction how much he cares about the sport and he is one of the hardest working players on tour.”
Dimitrov was clearly emotional as he left the court and with injuries continuing to trip him up, the 34-year-old must have questioned whether he will ever get a chance to beat the world No 1 at Wimbledon again.
There are also huge concerns for Sinner, who fell in the early stages of the match and appeared to hurt his elbow as he hit the turf.
He had lengthy treatment on the injury and was clearly in pain as the joint was being manipulated by the physio, with the consistency he always tends to show absent for much of this match after that fall.
It seemed as if an off-the-boil Sinner was there for the taking as Dimitrov continued to pound his serves in and keep the Italian off-balance.
That was before his cruel moment of ill-fortune struck and Sinner was handed a get-out-of-jail card that he so badly needed.
