Jannik Sinner was on the brink—but Wimbledon had other plans for the Italian World No. 1. On Monday, he faced off against Bulgarian Grigor Dimitrov, cruising into the match without dropping a set. Yet, trouble struck when Sinner appeared to suffer an elbow injury mid-match, forcing a medical timeout. Down two sets and staring at what looked like a tough exit, Sinner was up against Dimitrov, who was eyeing his first quarterfinal at Wimbledon since 2014. But fate had a twist in store.

Dimitrov’s hopes came crashing down in the third set. At 2-all, he served an ace, which earned a roar from the crowd before disaster struck. He suddenly froze, clutching his right pectoral muscle. The crowd fell silent as Sinner rushed over, concern etched on his face, while Grigor sank to the grass in pain. After a quick consultation with the on-court physio and a moment of reflection, Dimitrov made the heartbreaking decision to retire mid-match, ending his comeback bid on Centre Court.

This marked the Bulgarian’s fifth consecutive Grand Slam where he couldn’t finish a match—a tough streak that includes this year’s Australian and French Opens, plus last year’s Wimbledon and US Open. At 34, his body has repeatedly betrayed him on the sport’s biggest stages, turning potential triumphs into moments of frustration.

Before the match, Dimitrov sounded upbeat: “At the moment I feel great. I’m pain-free. I’ve done quite a sufficient amount of work before the tournament began. Overall, every day has been positive. I feel like I’m building off that, which makes me not only happy but excited for what’s to come,” He told the ATP website. His early play seemed to back that optimism. Aside from his face-off against Corentin Moutet, he had delivered straight-set victories!

Earlier in the match, Jannik Sinner had his own scare. He slipped hard behind the baseline in the opening game, landing awkwardly on his right arm. Despite grimacing through a medical timeout and receiving elbow treatment, the resilient Italian refused to back down. His coaches, Simone Vagnozzi and Darren Cahill watched nervously.

However, now Sinner is back in a fourth consecutive Wimbledon quarterfinal. Even if this wasn’t the way he’d hoped. He offered a comforting hand to the distraught Bulgarian and helped gather his gear as Dimitrov left the court to a warm round of applause, a tribute to his valiant effort.

Before facing Grigor Dimitrov, no player in Jannik Sinner’s draw had managed to take a set off the Italian. The 23-year-old had breezed through Luca Nardi, Aleksandar Vukic, and Pedro Martinez in straight sets at the Championships. On grass, he’s been rock-solid, winning over 85% of his service games. But Dimitrov made him stumble, and Sinner didn’t hesitate to tip his hat to the Bulgarian’s challenge.

Jannik Sinner offers kind words for Dimitrov after unexpected withdrawal

After helping Grigor Dimitrov with his bags, a visibly shaken Jannik took the mic for his post-match thoughts. “Honestly, I don’t really know what to say. Grigor is an incredible player—we all saw that today. He’s been so unlucky over the past couple of years. Not only is he a great player, but also a good friend of mine. We understand each other very well off the court, too. Seeing him in this position is heartbreaking. If there were any chance for him to play the next round, he would absolutely deserve it,” Sinner said, his voice full of genuine respect.

Their rivalry spans five matches, with Jannik Sinner holding a solid 4-1 lead. After losing their first encounter, he’s dropped just one set in the four wins that followed. They’ve crossed paths three times at Masters 1000 events and once in a Grand Slam, but Monday’s clash marked their debut on grass. Dimitrov’s sole victory came on clay in Rome back in 2020, where he edged out Jannik in a tight three-set battle.

Knowing Dimitrov’s injury struggles, Sinner’s empathy shone through. “But now, more than anything, I just hope he has a speedy recovery. It’s incredibly unfortunate from his side. I don’t take this as a win—it doesn’t feel like one. This is just a really sad moment for everyone who witnessed it. In the last few Grand Slams, he’s struggled a lot with injuries, and to see him dealing with that again is very tough. His reaction today showed just how much he cares about the sport. He’s one of the most hardworking players on tour, and it’s truly unfortunate what happened,” Jannik added, wrapping up a heartfelt moment amid the drama.

Now, the Italian heads into the quarterfinals to face Ben Shelton. These two have clashed six times before, with Jannik leading the head-to-head 5-1. They met earlier this year in the Australian Open semifinals, where Sinner came out on top, and again last year at Wimbledon’s round of 16, another win for the Italian.

While Jannik Sinner has made it through to the next round, his injury from this match still lingers. Could it pose a threat as he takes on the American on Wednesday, July 9? Share your thoughts below and stay tuned for all the Wimbledon twists and turns on our Live Blog!