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.

Tennis legend Roger Federer looked shell-shocked as a tearful Dimitrov walked over to the chair umpire to shake his hand. Sinner later said: "I don't take this as a win at all, this is just an unfortunate moment for all of us to witness.

The fourth-round clash between Jannik Sinner and Grigor Dimitrov ended in heartbreak for the latter, as the Bulgarian had to retire from the match during the third set, having taken a two-sets-to-love