WATCH: Heartbreaking scenes as Grigor Dimitrov breaks down in tears after tragic injury retirement vs Jannik Sinner at Wimbledon; Roger Federer watches on in concern

Grigor Dimitrov was playing brilliantly against Jannik Sinner at the 2025 Wimbledon Championships and was just one set away from pulling off a huge win. But luck wasn’t on his side, as a heartbreaking injury forced him to retire mid-match.

Dimitrov began his Wimbledon campaign with a confident win over Yoshihito Nishioka, followed by a victory against Corentin Moutet. He then defeated Sebastian Ofner to set up a fourth-round clash with top seed Sinner on Sunday, July 7, with his old rival Roger Federer watching from the stands on Centre Court.

The Bulgarian looked in complete control against Sinner, comfortably taking the first two sets and becoming the first player to take a set off the Italian at SW19 this year. But just after firing an ace to level the third set at 2-2, he suddenly collapsed to the ground clutching his right pec, prompting his opponent and two trainers to rush to his aid.

The 34-year-old was then helped to his chair for a medical timeout, breaking down in tears on the bench. With the score at 6-3, 7-5, 2-2, it was clear he couldn’t continue, and the match came to an emotional end. He then walked back onto the court, tears in his eyes, to bid a heartfelt goodbye.

Watch the video below:

Expand Tweet

Grigor Dimitrov’s situation was so heartbreaking that it left the entire crowd in shock. Jannik Sinner looked worried, and even Roger Federer appeared tense in the stands. To make matters worse, this marked Dimitrov’s fifth consecutive retirement from a Grand Slam.

Expand Tweet

About the author

Pritha is one of the driving forces behind Sportskeeda's tennis coverage, serving as an assistant content manager and editor. What began as a casual escape from her tiring biotechnology degree course in early 2022 has blossomed into a passion she loves, cherishes, and breathes every day.

Pritha’s love for the sport was spawned by her dad who showed her clips of "GOAT" Steffi Graf’s matches. Despite a thwarted dream of playing professionally due to injury, she finds solace in reporting the sport, while also mentoring other writers to ensure every article is error-free and top-notch. She double-checks credible sources, such as the tournament/player handles and big tennis media outlets, and gives proper credit where required.

Pritha's journey at Sportskeeda is marked by more than 2000 articles and close to 16 million views, with the "dream-come-true" moment of having her article shared by Chris Evert serving as a highlight of her career. A lifelong Wimbledon fan, Pritha also adores Rafael Nadal, Elena Rybakina, and Naomi Osaka.

When she's not seeking unique angles to elevate tennis coverage at Sportskeeda, she loves to channel her inner astrophysics "nerd" by exploring new sci-fi series and movies. A big Lionel Messi, Lewis Hamilton, and Randy Orton fan, she is always ready to engage in sports conversations anytime, anywhere, albeit not without a cup of coffee.

Know More

Who Are Roger Federer's Kids? Know All About Federer's Twins