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.

Dimitrov 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. After the conclusion of the match, Sinner addressed the Centre Court crowd.

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.