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

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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