Wimbledon: Devastated Grigor Dimitrov retires from Jannik Sinner clash as cruel Grand Slam injury curse continues

World number one Jannik Sinner progressed to the quarter-finals of Wimbledon courtesy of a heartbreaking injury to Grigor Dimitrov, who was two sets up against the top seed before being forced to cruelly retire from their last-16 match.

The 34-year-old Bulgarian was on the brink of eliminating the reigning US Open and Australian Open champion, roaring into a 6-3 7-5 lead and threatening an almighty surprise on Centre Court.

However, in the fourth game of the second set, Dimitrov began feeling his right pectoral muscle after hitting a backhand, although he carried on until the next point as he sought to saw out the game.

Dimitrov did so successfully with an ace, but the world number 21 then immediately sat down on the grass holding his chest, as Sinner came over to the Bulgarian's side out of concern for his opponent.

Dimitrov let out a couple of resigned laughs as the physios tried to work their magic, and the emotion was almost too much for the veteran player as he made his way off court in a bid for a miracle recovery.

The Bulgarian quickly re-emerged onto the court with tears in his eyes as he retired from the fourth-round match, thus sending Sinner through to a quarter-final showdown with the USA's Ben Shelton.

Dimitrov devastated as cruel retirement streak continues

Sport can be so cruel ?

Grigor Dimitrov is forced to retire despite being two sets up against world no.1 Jannik Sinner ?#Wimbledon pic.twitter.com/Fc2PHHfHTp

— BBC Sport (@BBCSport) July 7, 2025

One of the ever-popular players on the ATP Tour, the perennially luckless Dimitrov has just been unable to shake a cruel Grand Slam injury curse ever since last year's Wimbledon Championships.

Owing to Monday's injury, the 19th seed has now had to retire from each of his last five Grand Slam appearances, firstly calling it quits against Daniil Medvedev in last year's fourth round.

Dimitrov was then forced into a premature exit from his US Open quarter-final with Frances Tiafoe last year, before retiring in the second set of his Australian Open opener against Francesco Passaro.

The 34-year-old's rotten luck continued at Roland-Garros, as in his first-round showdown with Ethan Quinn, he had to bid farewell to the tournament due to a thigh problem.

Only a matter of weeks later, the injury gods have once again conspired against Dimitrov, who drew an incredibly concerned look from 20-time Grand Slam winner Roger Federer up in the Royal Box.

The Bulgarian deserved nothing less than the rousing reception he got from the Centre Court crowd, but that will come as little consolation after his body failed him on the biggest stage once again.

Written by
Ben Knapton