Grigor Dimitrov was leading two sets against world number one Jannik Sinner when he was forced to retire injured.
The Bulgarian tennis player led a fascinating match 6-3 7-5 2-2 when he fell to the grass and held his right pectoral after serving an ace.
He displayed visible signs of discomfort, prompting Sinner to rush over and lend a hand.
Dimitrov received immediate medical treatment after returning to his chair and then briefly left court before returning in tears to shake Sinner's hand.
This is not the first time the player had to leave the court in such devastating circumstances, as he retired injured from his first-round matches at the Australian and French Opens.
The conclusion of the match led the Italian player into the quarterfinals at SW19 for a second time.
Expressing his devastation on the match's situation, the 19-time ATOP tour title holder shared that this was "not the way we wanted it to end."
During the match, Sinner also took a medical timeout when he fell and suffered an apparent elbow injury, for which he is set to receive an MRI on Tuesday, July 8.
"It was an unfortunate fall - I checked the video and it didn't seem a tough one but I still felt it a lot during serve and forehands especially," he told the press conference.
Dimitrov was the first seeded player Sinner had faced this Wimbledon, which gave the spectators an exciting exchange to witness as both the players tried to match each other's skills.
Notably, Grigor Dimitrov is the player with the most quit ATP Tour matches, as he was forced to retire injured from 12 games.
