Dimitrov was playing fantastic tennis, running Sinner around the court and delivering booming serves. Dimitrov won the first set 6-3 and survived a hard-charging comeback attempt from the Italian in the second to take the set 7-5 and put the world No. 1 in a desperate position.

Dimitrov most recently retired from the first round of the French Open with a thigh injury while holding a 6-2, 6-3, 2-6 lead over American Ethan Quinn. He retired from Wimbledon in the fourth round in 2024 with an abductor tear. He trailed Daniil Medvedev, 5-3 in the first set at the time of that injury.

Grigor Dimitrov was up two sets to none on world No. 1 Jannik Sinner on Monday at Wimbledon, but was forced to retire due to an injury. His retirement was agonizing to watch as the 34-year-old Bulgarian bowed out despite having an incredible chance to knock off Sinner.