Jannik Sinner endured a dramatic fourth-round match at Wimbledon 2025, ultimately advancing to the quarter-finals after Grigor Dimitrov was forced to retire due to injury. The world No. 1 suffered a fall early in the match and found himself trailing by two sets before Dimitrov's unfortunate exit.

The match began with a worrying moment for Sinner, as he fell heavily in the first game while attempting to reach a backhand. He landed on his right arm and subsequently dropped his serve in the following game. Dimitrov, displaying a crafty game with slices and drop shots, took the first set 6-3. The Bulgarian continued to put pressure on Sinner, winning the second set 7-5. Dimitrov won the first two sets, becoming the first player to take a set off Sinner at the Championships.

After the second set, the roof on Centre Court was closed due to fading light, causing a 10-minute delay. In the third set, with the score at 2-2, Dimitrov served an ace but then collapsed to the ground, clutching his right pectoral muscle. Sinner rushed to his aid as Dimitrov was helped to his chair, visibly in distress. The 34-year-old Bulgarian briefly went off-court for treatment but was unable to continue, retiring from the match in tears.

Sinner expressed his sympathy for Dimitrov, acknowledging the unfortunate nature of his opponent's retirement. "I hope he has a speedy recovery. It's very unlucky from his side,” Sinner said. “I don't take this as a win at all". This marks Dimitrov's fifth consecutive Grand Slam appearance ending in retirement. His injury woes began at Wimbledon 12 months ago, where he slipped and damaged his knee in the fourth round against Daniil Medvedev.

Despite the circumstances of his victory, Sinner is now through to his fourth consecutive Wimbledon quarter-final. He will face Ben Shelton in the quarter-finals. Shelton advanced to his first Wimbledon quarter-final by defeating Lorenzo Sonego in four sets. The American had previously bested Sonego at the Australian and French Open.

Other quarter-final matchups include Novak Djokovic against Flavio Cobolli. Cameron Norrie, the last remaining British singles player, will face Carlos Alcaraz. Alcaraz is aiming for his third consecutive title at SW19.