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. 

CLICK HERE FOR MORE SPORTS COVERAGE ON FOXNEWS.COM

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.

BEN SHELTON TAKES 1 MINUTE TO DEFEAT OPPONENT AT WIMBLEDON AFTER MATCH WAS SUSPENDED DUE TO DARKNESS

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.

"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.

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. 

Follow Fox News Digital’s sports coverage on X, and subscribe to the Fox News Sports Huddle newsletter.