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.

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.

Former World No.3 Grigor Dimitrov was in prime position to upset top seed Jannik Sinner in the round of 16 at the 2025 Wimbledon Championships. However, the Bulgarian would suffer a devastating injury during the match,