Dimitrov-Sinner: An Iconic Wimbledon Upset That Wasn’t

Jannik Sinner (photo: Wimbledon video)

WIMBLEDON/WASHINGTON, July 8, 2025 (by Michael Dickens)

After a week of upsets that has defined the 138th edition of the Wimbledon Championships, there are plenty of big names that are still standing. Among them are two-time defending champion Carlos Alcaraz and women’s top seed Aryna Sabalenka. Plus, there’s men’s top seed Jannik Sinner. Barely.

Monday evening, before a full house of 15,000 fans that filled Centre Court at the All England Club, the World No. 1 Sinner was on the verge of exiting the grass-court major. He was down two-sets-to-none to No. 17 seed Grigor Dimitrov. All of a sudden, at 2-all in the third set – and shortly after the roof was closed at the end of the second set due to fading daylight – Sinner became the beneficiary of the worst kind of good luck imaginable: Dimitrov injured himself and couldn’t continue. He retired due to a pectoral muscle injury.

First, though, it’s necessary to go back to the beginning of the match in order to set up the surprising – albeit heartbreaking – conclusion. During the seventh point in the first game, Sinner lost his footing, slipped and fell. He braced the fall with his right hand while still holding his racquet and appeared to injure his right elbow. He took a medical timeout and received a pain-relieving medication during the change-over after the fifth game in the second set. Then, he left the court before the start of the third set. Throughout, as he soldiered on, he shook his right arm and rubbed his elbow in between points.

Soon, Sinner found himself trailing 6-3, 7-5 to Dimitrov, after the 34-year-old Bulgarian had put on a sensational performance that included serving 13 of his eventual 14 aces and striking 31 of his total 36 winners. Additionally, Dimitrov effectively won points at the net as well as from the baseline. Sinner looked lost and confused, ripe for an upset.

Then, early in the third set, Dimitrov hit the last of his 14 aces and seemed to injure his right pectoral muscle in leveling the score at 2-all. Dimitrov collapsed to the court with a grimacing look on his face as he grabbed at his chest with his left hand. He sat there, saying “My pec, my pec.”

While there was a hint of laughter from Dimitrov, there was shock, too. Soon, Sinner came around the net to his aid and rescue, kneeling by Dimitrov’s side. Moments later, the 23-year-old Italian helped his close friend to his chair on the sideline.

Quickly, a trainer and doctor came to check on Dimitrov as Sinner remained close. After a few minutes, a medical time out was called by the chair umpire and Dimitrov was helped off the court by the medical team. Meanwhile, Sinner remained behind and eventually began hitting a few practice serves to pass the time.

A few minutes later, Dimitrov returned to Centre Court with tears in his eyes. It was evident he would be unable to resume. He made his way to the chair umpire and retired from his match with Sinner, all the while needing to win just four more games to pull off the biggest upset at this year’s Wimbledon.

It was the fifth straight Grand Slam that Dimitrov had needed to retire due to injury. His streak of misfortune dates back to last year’s Wimbledon and US Open, then continued earlier this year at the Australian Open in January and the French Open in May.

Talk about bad luck befalling one of the nicest and most competitive players on the ATP Tour, admired by his peers and beloved by tennis fans worldwide. Dimitrov has reached three major semifinals – at Wimbledon in 2014, at the Australian Open in 2017 and at the US Open in 2019. In a total of 59 Grand Slam appearances, though, Dimitrov has never reached a final.

With eight-time Wimbledon champion Roger Federer watching from the Royal Box, Sinner looked stunned as he briefly addressed the crowd during his on-court interview. He had just helped carry Dimitrov’s racquet bag off the court.

“I don’t know what to say, because he is an incredible player,” Sinner said. “I think we all saw this today. He’s been so unlucky in the past couple of years. An incredible player. A good friend of mine also; we understand each other well off the court, too. Honestly, if there would be a chance that he could play the next round, he would deserve [it]. … I don’t take this as a win at all; this is a very unfortunate moment to witness for all of us.”

Later, Sinner said he would get an MRI exam on Tuesday to rule out a serious injury to his right elbow. Assuming he’s cleared to play on, Sinner would face No. 10 seed Ben Shelton of the United States, who reached his first Wimbledon quarterfinal with a 3-6, 6-1, 7-6 (1), 7-5 win over No. 47 Lorenzo Sonego of Italy on No. 1 Court, on Wednesday.

Around the All England Club

The first two men’s and women’s quarterfinals take place on Tuesday. Two-time defending champion and this year’s No. 2 seed Carlos Alcaraz of Spain will face British No. 1 Cameron Norrie, ranked 61st, in the second match of the day on Centre Court. It follows No. 1 seed Aryna Sabalenka of Belarus versus 104th-ranked Laura Siegemund of Germany. On No. 1 Court, play begins with No. 5 seed Taylor Fritz of the United States against No. 17 seed Karen Khachanov of Russia, followed by No. 13 seed Amanda Anisimova of the United States versus No. 50 Anastasia Pavlyuchenkova of Russia.

Monday’s Wimbledon results

Tuesday’s Wimbledon order of play

By the numbers

When Cameron Norrie faces defending champion Carlos Alcaraz on Tuesday, it will mark the 20th meeting between a British player and the men’s singles defending champion at Wimbledon in the Open Era. British players have won just two of those previous 19 meetings – the last one came when Tim Henman defeated Richard Krajicek in the round of 16 in 1997.

“Quotable …”

“He is a good friend of mine. We all saw from his reaction how much he cares. He is one of the most hard-working players on tour. This is not the end we wanted to see. We all wish him only the best. Let’s give all our applause for him.”

– Top seed Jannik Sinner of Italy, during his on-court interview speaking of Grigor Dimitrov, who retired from their fourth-round match due to injury.