Grigor Dimitrov heartbreakingly retired from his Round of 16 Wimbledon match vs. World No. 1 Jannik Sinner due to injuring a pectoral muscle on a volley during the third set. Dimitrov held a 2–0 lead through two sets against 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.