Grigor Dimitrov was cruising toward the biggest win of his season. Two sets up against world number one Jannik Sinner at Wimbledon on Monday, the Bulgarian looked unstoppable. Then one serve changed everything. Dimitrov hit an ace to tie the third set at 2 games apiece, but collapsed to the ground clutching his chest. What happened next left tennis fans heartbroken and raised serious questions about his future.
What Did Andy Roddick See in Dimitrov’s Injury?
Former world number one Andy Roddick watched the match unfold and knew immediately that something was seriously wrong. The American didn’t hold back when breaking down what he witnessed.
“He hit and I go, ‘Guys, this is over.’ Like this was instant,” Roddick said on his podcast. “You can’t hide from like a pectoral muscle on a serve. You literally when you reach back, you kind of have to let it rip from there.”
Roddick’s medical assessment was blunt. “It’s probably a torn pec. This is me playing doctor and I’m not. Best case scenario, it’s a pull. Worst case, it’s a tear. That’s not a quick thing to get over.”
Beyond the injury itself, Roddick emphasized what makes this situation so tough for tennis fans. He praised Dimitrov’s character, saying: “One of the most well-liked guys on tour, one of the most respected. He has a reputation as an incredibly professional hard worker.”
The timing couldn’t be worse for the 34-year-old Bulgarian[VERIFIED, BUT DOUBLE-CHECK | Google: Grigor Dimitrov age 2025 | StatMuse: grigor-dimitrov-age-2025 | Perplexity: Grigor Dimitrov age 2025]. As Roddick pointed out: “He’s not young anymore. He’s had to retire in the last five grand slams.”
What made this retirement particularly crushing was the opportunity that slipped away. Roddick explained: “It was just heartbreaking for many reasons. One, the opportunity of not getting to finish off the world number one on the greatest court in all of tennis. Like he’s at the point where he wants that last big moment.”
The former US Open champion also shared the darker thoughts that must be going through Dimitrov’s mind. “I guarantee the last time I played Wimbledon, I didn’t know if I was going to retire. But like I guarantee you that’s a thought for him. This is a bad injury. Will I be back here? Is this the way my Wimbledon story ends?”
How Bad Is Dimitrov’s Grand Slam Retirement Record?
This latest setback continues a devastating pattern for Dimitrov at tennis’s biggest tournaments. The Bulgarian has now retired from five straight Grand Slams, a streak that began at Wimbledon 2024 against Daniil Medvedev. The painful sequence continued through the US Open 2024, Australian Open 2025, French Open 2025, and now Wimbledon.
The numbers tell an even grimmer story. Dimitrov now holds the record for most Grand Slam retirements in the Open Era with 10 total, surpassing other players including Novak Djokovic, who has 6 Grand Slam retirements in his career.
What makes Monday’s retirement so frustrating is how well Dimitrov was playing before the injury struck. He dominated Sinner in the opening two sets, winning 6-3, 7-5Â and looking completely in control. His slice was working perfectly, and his serve was giving the world number one serious problems.
Worrying scenes in the Grigor Dimitrov & Jannik Sinner match at Wimbledon.
Grigor hurt his pectoral muscle while hitting a volley.
He’s laughing out of hysteria. pic.twitter.com/32MPh0OXjt
— The Tennis Letter (@TheTennisLetter) July 7, 2025
Instead of celebrating a career-defining victory, Dimitrov was forced to retire once again, ending what could have been his greatest Wimbledon moment in the most heartbreaking way possible.
