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The career of Grigor Dimitrov has been defined in a way by bad injury luck, but nothing stacks up to what happened on Monday at Wimbledon. The Bulgarian was putting on a vintage performance against World No. 1 Jannik Sinner, taking the first two sets to build a commanding lead and set the stage for a monster upset.
Then, as it so often has for Dimitrov over the course of his career, disaster struck. Following a serve at 1-2 in the third set, Dimitrov hit an awkward backhand slice and appeared to grab his pectoral muscle. On his next first serve, which was fired for a winner to seal the game, he crumpled to the ground holding it.
Sinner quickly came over to check on Dimitrov, who then took a medical timeout as doctors attended to him. However, his worst fears were confirmed and he was forced to retire from the match leading the top seed, 6-3 7-5 2-2.
Dimitrov has not gotten injured and been forced to retire at each of the last five majors, including the fourth round of Wimbledon 2024 against Daniil Medvedev. He was also in a close battle with Frances Tiafoe in the U.S. Open quarterfinals before being forced to pull out last fall.
After struggling with injuries and failing to find much form for a lot of the 2025 campaign, Dimitrov was just four games from one of the biggest wins of his career before the injury bug tragically struck again.
It's a good stroke of luck for Sinner, who was struggling with a right arm injury throughout the match after taking a hard fall early on in the first set. He now advances to the Wimbledon quarterfinals for the fourth consecutive year to take on No. 10 seed Ben Shelton in a rematch of last year's fourth round.
Even though he is moving on, Jannik Sinner isn't taking this as a victory for himself after his good friend went down.
"I don't take this as a win at all."
Jannik Sinner was full of respect for his friend Grigor Dimitrov after he was forced to retire.#Wimbledon pic.twitter.com/bQTsxUM8Mu
— Wimbledon (@Wimbledon) July 7, 2025
“I don't know what to say because he is an incredible player, I think we all saw this today,” Sinner said after the match. “He has been so unlucky in the past couple of years. An incredible player, good friend of mine also. We understand each other very well off the court too. Seeing him in this position, honestly if there was a chance he could play the next round, he would deserve it. I hope he has a speedy recovery.
“Very unlucky from his side. I don't take this as a win at all. This is just a very unfortunate moment to witness for all of us.”
Sinner's quest for a first Wimbledon remains alive, while Dimitrov will likely head home to have further tests done before the summer hardcourt swing gets going in North America.
