Taylor Fritz’s latest clash with Novak Djokovic at the US Open brought plenty of intrigue on court, but it was his choice of attire that had fans talking as much as the tennis.
During his quarter-final appearance under the lights of Arthur Ashe Stadium, eagle-eyed viewers spotted Fritz’s trademark Hugo Boss headband flipped upside down.
The embroidered “BOSS” logo, which usually sits prominently across his forehead, instead appeared as “SSOB” — an unintentional slip that quickly spread across social media.
Some fans joked it was an attempt to reverse his fortunes against Djokovic, a player he has never beaten in his career so far.
Taylor Fritz was powerless to prevent his defeat to Novak Djokovic at the US Open on Tuesday night
|REUTERS
Others suggested it was simply an oversight on the part of the 27-year-old American, who admitted ahead of the tournament that he felt the pressure of carrying home hopes deep into the final Grand Slam of the year.
For Hugo Boss, however, the gaffe will have raised eyebrows.
The German fashion giant reportedly pays Fritz around $7 million-a-year to showcase their brand on tennis’s biggest stages.
And there are few stages bigger than a US Open quarterfinal against Djokovic, a 24-time Grand Slam champion chasing history.
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For Boss, their premium advertising moment was instead broadcast in reverse to millions around the world.
Fritz, who is still seeking his first major title, has often been touted as the man most likely to end the American men’s Grand Slam drought that stretches back to Andy Roddick’s triumph in New York in 2003.
But against Djokovic, he once again came up short.
The Serb’s relentless returning and big-point mastery proved too much, despite Fritz raising his level after a shaky start.
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Another great run in New York for Taylor Fritz! 👏 pic.twitter.com/MztjM8J9Tk
— US Open Tennis (@usopen) September 3, 2025
While Djokovic advanced to yet another semi-final, Fritz’s quest for a first major of his career continues.
At 27, he still has time to write his name into Grand Slam history, but with Djokovic and a new wave of champions like Carlos Alcaraz and Jannik Sinner dominating the scene, the challenge remains immense.
Meanwhile, Djokovic was asked about being the underdog at a time when Alcaraz and Sinner are dominating the scene.
And the 38-year-old is relishing that label, admitting that he wants to 'mess up the plans of most people' by dumping Alcaraz out in the last four.
"We don't need to spend words about two of them," the former world No 1 said.
"We know that they are [the] two best players in the world.
"Everybody is probably expecting and anticipating the finals between two of them. I'm going to try to, you know, mess up the plans of most people.
"Let's see. You know, Sinner still has to win a couple of matches to get to the finals. But they are playing definitely the best tennis of any player here. They have been [the] dominant force since the beginning of the tournament.
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Taylor Fritz is yet to beat Novak Djokovic during his career
|REUTERS
"But, you know, I definitely am not going with a white flag on the court. I don't think anybody does really when they play them, but particularly not me.
"I put myself in another semi-finals of a Grand Slam this year. I have been very consistent, most consistent on Slams this season, and that's what I said at the beginning of the year, where I would like to perform my best tennis and make the best results.
"Here we are. I have another chance, another shot. Hopefully, as I said, I can be fit enough and play well enough to keep up with Carlos. Then it can be anybody's match."