Grigor Dimitrov's promising Wimbledon upset bid against Jannik Sinner ends in heartbreaking injury retirement

Grigor Dimitrov was one set away from upsetting Wimbledon’s No. 1-seeded men’s singles player, Jannik Sinner, on Monday. 

But an untimely injury changed all of that.

Dimitrov had to retire from the match in the Round of 16 due to an apparent pectoral injury despite owning a 6-3, 7-5, 2-2 lead over Sinner. 

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Grigor Dimitrov of Bulgaria gets an injury in the Gentlemen's Singles Fourth Round match against Jannik Sinner of Italy on day eight of The Championships Wimbledon 2025 at All England Lawn Tennis and Croquet Club on July 0, 2025 in London, England. (Shi Tang/Getty Images)

In turn, Sinner is heading to the Wimbledon quarterfinals. 

During a serve, Dimitrov immediately fell on the grass court in pain, grabbing at his right pec. Trainers sprinted out to help him, and it appeared all Dimitrov could do was laugh in the moment, knowing his potential upset was chalked.

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Still, Dimitrov’s status was up in the air as he left the court for a medical timeout. However, when he returned to the court, he shook Sinner’s hand to say that he couldn’t continue. 

The serve was the set-tying point, as Dimitrov won the fourth game of the third set. 

The Centre Court crowd gave Dimitrov a loud ovation despite the circumstances, while he packed his bag to leave the match and the tournament.

"I don’t take this as a win at all," Sinner said after the match, showing respect to Dimitrov in the process.

Jannik Sinner (L) of Italy greets Grigor Dimitrov of Bulgaria after Dimitrov retired due to injury in the Gentlemen's Singles Fourth Round match on day eight of The Championships Wimbledon 2025 at All England Lawn Tennis and Croquet Club on July 07, 2025 in London, England. (Shi Tang/Getty Images)

"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."

Dimitrov was playing well at Wimbledon, where he was hoping to reach the semifinals for the first time since 2014 — his deepest run in the tournament to date. 

But injury has been an issue for Dimitrov, especially in Grand Slams. This is the fifth straight tournament he has been forced to retire, most recently occurring in the French Open due to a thigh ailment in the first round. 

In 2024, he left the fourth round with an abductor tear during his match against Daniil Medvedev.

Grigor Dimitrov of Bulgaria is crying after he retired during Day Eight of The Championships Wimbledon 2025 at All England Lawn Tennis and Croquet Club on July 7, 2025 in London, United Kingdom. (Marleen Fouchier/BSR Agency/Getty Images)

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Despite not accepting it as a win, Sinner will have to prepare for his quarterfinals matchup with American phenom Ben Shelton, the No. 10 seed of the tournament. Shelton defeated Lorenzo Sonego 3-6, 6-1, 7-6, 7-5 on Monday. 

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