Grigor Dimitrov was in tears as he left Wimbledon. 

Dimitrov’s bid to upset world No. 1 Jannik Sinner came to a heartbreaking end in the third set of their Round of 16 match, with the Bulgarian tennis player having to retire from the match due to an injury to his right pectoral muscle. 

He had taken the first two sets of the match — 6-3, 7-5 — and was tied with Sinner 2-2 in the third when he started feeling the injury while serving. 

Dimitrov could be seen saying “my pec,” and after the serve, he quickly grabbed at the area in pain. 

Trainers looked at Dimitrov on the sideline and he was in tears before he walked off the court to receive further inspection, only to return moments later, shaking his head to indicate he could play no further. 

It marked the fifth consecutive Grand Slam that Dimitrov was forced to retire. 

“I don’t know what to say. He is an incredible player, we all saw this today. He’s been so unlucky in the past couple of years,” Sinner said during his postmatch interview on the court. 

“An incredible player and a good friend of mine also. We understand each other well off the court, too. Seeing him in this position, honestly, if there could be a chance he could play in the next round, he would honestly deserve it. But now mostly I hope he has a speedy recovery, very unlucky from his side. I don’t take this as a win at all. This is a very unfortunate moment for us to witness.” 

Grigor Dimitrov clutches his chest with an injury which forced him to retire. AP

Grigor Dimitrov receives medical attention after suffering an injury during the third set of his Wimbledon match against Jannik Sinner on July 7, 2025. Getty Images

He added: “I think already in the last grand slams he struggled with injuries, seeing him with this is very tough, his reaction, how much he cares about the sport, he’s one of the most hard working on tour. It’s very sad.” 

Sinner has his own injury concern to deal with. He hurt his elbow when he fell early in the match, requiring an injury stoppage. 

Sinner said he will have an MRI exam Tuesday on his elbow “to see if there’s something serious” and added in Italian: “There is some concern.” 

Jannik Sinner (l.) helps Grigor Dimitrov to his bench after suffering an injury during their Wimbledon match on July 7, 2025. Getty Images

This was the second consecutive year Dimitrov had to retire from a match at Wimbledon, following an abductor tear in his leg which forced his exit last year. 

“He served incredibly well, very precise. Also very fast. Changed up the game very very good,” Sinner said. “It was a bit breezy. He used the wind in the best possible way. He prepared the match in a very good way and executed even better. He was playing some great tennis. After with the roof closed, you don’t know what’s happening. There were some good rallies in the beginning of the third set. I tried to stay there mentally. I broke him back at 5-4. Then he played lights out tennis again to break me back. I think he’s showing his potential. It’s very unfortunate, as I said on court. I wish him a speedy recovery.” 

Dimitrov walked off the court Monday to loud cheers from the crowd as Sinner helped him carry his bag back to the locker room. 

Jannik Sinner plays a forehand return to Bulgaria’s Grigor Dimitrov. AFP via Getty Images

That’s when the emotions really started to flow for Dimitrov. 

Sinner advanced to the quarterfinals as he looks for his first Wimbledon title and attempts to put his heartbreak at the French Open final — when he lost in five sets to Carlos Alcaraz after taking the first two sets — behind him. 

If Sinner can play in the quarterfinals Wednesday, he will take on American Ben Shelton, who reached his first Wimbledon quarterfinal — doing a round better than his father-turned coach, Bryan, did in 1994 — by beating Lorenzo Sonego 3-6, 6-1, 7-6 (1), 7-5 on Monday. 

Italy’s Jannik Sinner checks on Bulgaria’s Grigor Dimitrov after he went down with an injury during a fourth round men’s singles match at the Wimbledon Tennis Championships. AP

Shelton, a 22-year-old American who won the 2022 NCAA singles title for the University of Florida, improved to 3-0 against Italy’s Sonego in Grand Slam action this season. It’s the first time two men faced each other in a year’s initial three majors since John McEnroe went 3-0 against Jimmy Connors in 1984. 

Novak Djokovic and Flavio Cobolli also won their matches Monday and will meet in another quarterfinal Wednesday.

— With AP