Jannik Sinner is now in the Wimbledon quarterfinals, albeit not in the way he had hoped. Sinner lost the opening two sets to Grigor Dimitrov, who had to retire because of an apparent pectoral injury.

Dimitrov displayed remarkable skill, both serving and navigating the court expertly. He took the first set 6-3 and managed to fend off a fierce comeback attempt in the second to win it 7-5, placing Sinner in a precarious spot.

Regrettably for Dimitrov, who has had a tumultuous history with injuries, one of his powerful serves caused him to clutch his chest. He was briefly able to keep playing, but soon collapsed in discomfort on the grass, prompting an intervention from Sinner and medical staff.

Dimitrov’s injury Getty Images

Dimitrov continued his match under pain but ultimately had to leave the court for medical assessment, returning in an emotional state, visibly upset.

This incident marked the fifth time Dimitrov had to withdraw from a Grand Slam due to injury in recent events, including:

• 2024 Wimbledon – Fourth round
• 2024 US Open – Quarterfinals
• 2025 Australian Open – First round
• 2025 French Open – First round
• 2025 Wimbledon – Fourth round

Despite not performing at his peak, Sinner expressed regret over the result and concern for his friend.

“Honestly, I don’t know what to say because he’s an incredible player. I think we all saw that today. He has been so unlucky the past couple of years. An amazing player and a good friend of mine. Seeing him in this position, I feel he deserves the chance to play the next round if possible. I mostly hope for his speedy recovery. I don’t see this as a win at all. It’s just an awful moment to witness for all of us,” Sinner shared.

Now, Sinner is set to face American Ben Shelton in the quarterfinals, facing his own physical challenges as he has been experiencing discomfort in his right arm during the tournament.