Incredible injury tragedy: Cruel end: Dimitrov's bitterest tears shock Wimbledon

Grigor Dimitrov beats world number one Jannik Sinner at Wimbledon, but then comes the shock: a serious chest injury brings a gruesome end. Dimitrov breaks down in tears, as his injury history takes on tragic traits.

Roger Federer can barely look. His gaze speaks volumes. The tennis legend is a spectator in the Royal Box on Center Court at Wimbledon on Monday evening, and his utterly shocked expression sums up what Grigor Dimitrov is currently experiencing on the grass court. It's one of the most heartbreaking moments tennis has seen in recent years.

The Bulgarian initially stunned Federer and the rest of the crowd by winning the first two sets of his quarterfinal match at Wimbledon against world No. 1 Jannik Sinner. Dimitrov led 6-3, 7-5, and 2-2 in a thrilling round of 16 match – then disaster struck. Dimitrov was forced to retire in tears due to a suspected pectoral muscle injury, and Federer could barely watch.

Grigor Dimitrov has everything under control against Sinner and is on the verge of one of the biggest upsets at Wimbledon. The 34-year-old is playing some of the best tennis of any professional this year – he's particularly impressive with his one-handed backhand, which has almost disappeared since Federer retired – and has dropped only one set in all his matches. But world number one Sinner hadn't lost a single set before the match and is the favorite going into the clash, and that's not the only reason he does so.

Dimitrov collapses

But Dimitrov blasted the Italian with powerful and precise serves from the start, playing versatile and perfect grass tennis. He hit 14 aces, Sinner only four. But then, of all things, an ace serve brought the drama. It was just a small movement. A backswing on a serve, the kind tennis players repeat hundreds of times a day. But suddenly, Dimitrov grabbed his right pectoral muscle, contorted in pain.

The tragedy unfolds in a flash. The Bulgarian falls immediately to the ground, laughing in shock and pain, and appears to be having trouble breathing. Sinner immediately rushes to his side; the two are good friends off the court. A minute-long injury break follows, and a physio examines Dimitrov's chest, who is already close to tears.

The tennis pro briefly leaves the court, perhaps for treatment, a last glimmer of hope. But the Bulgarian immediately returns to the grass, collapses, and begins to cry. Sinner takes the wretched little heap in his arms, grabs his bags, and carries them off the court for him. Dimitrov can barely raise his arm to wave to the stunned audience, who give him a long standing ovation.

Sinner knows he was the weaker player that day and probably wouldn't have won. In the "winner's" interview on court, he doesn't want to talk about the match, but simply explains how bitter the whole thing is for his friend Dimitrov and that he wishes him a "speedy recovery." In a cruel twist of fate, Sinner also took a medical timeout midway through the second set due to an elbow injury. He had appeared unwell after a fall. The Italian will undergo an MRI scan this Tuesday to determine the severity of the injury.

Bitter injury tragedy

Particularly tragic for Dimitrov: This is the fifth consecutive Grand Slam tournament in which he has to withdraw due to injury. The Bulgarian most recently exited the French Open with a thigh injury in the first round, while leading 6-2, 6-3, and 2-6 against American Ethan Quinn. In 2024, he involuntarily left the court in the fourth round of Wimbledon with a torn adductor muscle. In between, Dimitrov also withdrew from the 2024 US Open and the 2025 Australian Open. No player has withdrawn more times from ATP Tour matches due to injury since the start of the 2020 season (12). The injury prevents him from achieving his best performance at Wimbledon since reaching the semifinals in 2014.

After this injury-plagued season, Dimitrov expressed shortly before the clash with Sinner how grateful he was to be healthy and pain-free in the round of 16 against the world No. 1. "I'm here to play. I feel great. After three matches, I'm in good physical shape, which gives me a positive and optimistic attitude to go out there and play my game," said the 34-year-old. "The rest is fun. That's important. We're in the second week of Wimbledon. Let's have fun."

Now the incredibly dramatic series of misfortunes continues for the man who was once nicknamed "Baby Fed" for his playing style, which resembles that of eight-time Wimbledon champion Roger Federer. Grigor Dimitrov saw Federer's worried look from the Royal Box once again on Monday as he staggered off the hallowed turf. Then his tournament came to the bitterest of all endings.