Pressure was sky-high for Taylor Fritz heading into his quarterfinal showdown with Novak Djokovic at the US Open, but a wardrobe blunder stole the spotlight; at least for a few hilarious moments.
Instead of showing off his Hugo Boss sponsor, Fritz walked out onto Arthur Ashe Stadium with his headband flipped. The “BOSS” logo became “SSOB.” The gaffe soon exploded across social media, getting laughs from fans, fellow players, and Fritz himself once the match ended.
How Did Fans and Fellow Players React to Taylor Fritz’s Headband Blunder?
Right in the middle of one of the biggest matches of his career, the 27-year-old American spent the first two sets sporting the upside-down headband before fixing it. By then, though, the internet was all over it.
Djokovic ultimately reminded everyone why he’s the king of these courts, rolling through with a 6-3, 7-5, 3-6, 6-4 win. He stretched his winning streak over Fritz to 11-0, but the headband misstep got just as much buzz as the four-set slugfest, quickly becoming one of the US Open’s most viral stories.
Fritz wasn’t shy about joining the fun. After the match, he posted on X, “Yo why’d nobody tell me that s**t was backwards.”
Yo why’d nobody tell me that s**t was backwards
— Taylor Fritz (@Taylor_Fritz97) September 3, 2025
Retired Canadian tennis star Eugenie Bouchard joined in with a post of her own: “Taylor Fritz’ headband was on upside down on purpose right?”
Taylor Fritz’ headband was on upside down on purpose right?
— Genie Bouchard (@geniebouchard) September 3, 2025
Fans were quick with their own jokes. One posted, “More sobbing than bossing, it makes sense.” Another chimed in, “HE TURNED THE HEADBAND AROUND.”
More sobbing than bossing, it makes sense
— Tony Lascari (@lascari_tony) September 3, 2025
HE TURNED THE HEADBAND AROUND
— Served with Andy Roddick (@Served_Podcast) September 3, 2025
One user even shared a photo with Fritz flipped upside down so the words finally read “BOSS.”
Adjusting Taylor Fritz#headband #djokovic #USOpen2025 pic.twitter.com/XdCR6IiRwG
– Andrea Guglieri (@AndreaGuglieri) September 3, 2025
The memes just kept coming, with posts like “Bro was doomed from the start, lol” and “Next time, bring your mirror in your wallet. 🧠”
What Does Taylor Fritz’s US Open Run Say About His Rivalry With Novak Djokovic?
With the loss in the quarterfinals, Fritz capped his 10th year playing in New York. The 2024 runner-up and this year’s number four seed powered past Emilio Nava, Lloyd Harris, Jérôme Kym, and 21st seed Tomáš Macháč to make it to his third straight quarterfinal here.
Djokovic has dominated his rivalry with Fritz, allowing the American tennis star to claim just four sets across their 11 encounters. Two came during their five-set clash at the 2021 Australian Open, another in their four-set quarterfinal meeting at the 2024 Australian Open, and the most recent in the 2025 US Open quarterfinals, which Djokovic also won in four. The Serbian has closed out straight-set victories in all nine of their other matches.