Jannik Sinner made history by winning the 2025 Wimbledon Championships, defeating arch-rival Carlos Alcaraz in the final on Sunday, July 13. But what many fans couldn’t help but recall was Grigor Dimitrov’s near-upset of the World No. 1 in the fourth round, a match that came incredibly close to shifting the course of the tournament.
Sinner and Alcaraz had set up a rematch of their epic French Open final from just a month ago, where Alcaraz had come out on top after a five-set thriller. But this time, the tide turned in the Italian’s favor. Despite dropping the first set, he rallied brilliantly to win 4-6, 6-4, 6-4, 6-4 and claim his first Wimbledon title.
Sinner’s road to the final was anything but smooth, with his toughest test coming in the fourth round against Dimitrov. The Italian was struggling with an elbow issue and had dropped the first two sets, but the match took an unexpected turn when Dimitrov suffered a serious pec injury and was forced to retire, handing his opponent a walkover victory just when things looked most uncertain.
Fans have now taken to X to speculate what might have happened if Grigor Dimitrov had managed to close out his match against Jannik Sinner. One user wrote:
"Wonder what Grigor Dimitrov is thinking right now..."
"Grigor Dimitrov's pec changing the course of tennis history was not on my bingo card for this fortnight," another wrote.
One account posted:
"This is just sport and we will have to live with the unknown forever. Sinner very much earned this Wimbledon with his great tennis, but must still say thoughts and commiserations to Grigor Dimitrov and everyone around him."
"Grigor Dimitrov really could've won Wimbledon, eh?" one user wondered.
"The biggest mystery this entire tournament... and will go down in history as a HUGE 'What if?' How did Grigor Dimitrov take two sets off this guy?" another joined in.
One account tweeted:
"Should Jannik Sinner now play Grigor Dimitrov for the #Wimbledon title when he recovers from surgery?"
Jannik Sinner sends consoling message to Grigor Dimitrov after Bulgarian's injury heartbreak at Wimbledon

Jannik Sinner was trailing 3-6, 5-7, 2-2 when Grigor Dimitrov was forced to retire due to a heartbreaking injury during their fourth-round clash at the Wimbledon Championships. Despite the circumstances, the moment between the two was touching, as the Italian showed genuine concern, hugging the Bulgarian and even helping him off the court, to the crowd's warm round of applause.
Later, during his on-court interview, Sinner addressed the situation with empathy, sending a heartfelt message to Dimitrov. He called the injury “very unlucky” and added that he didn’t want to think of the result as a true win.
"Very, very unlucky from his side, I don’t think of this as a win at all, this is just a very unfortunate moment to witness for all of us," the World No. 1 said.
"I think already in the last Grand Slams he’s struggled a lot with injuries and seeing him now again having this kind of injury, it’s very very tough and we all saw this with his reaction, how much he cares about the sport," he added.
He later took to X and posted:
"Get well soon, my friend. Wishing you all the best @GrigorDimitrov."
With the Wimbledon trophy now in his hands, Jannik Sinner has secured two of the three Grand Slam titles so far this year. He’ll now turn his attention to the North American hardcourt swing before aiming to defend his US Open title in August.