US Open: Upsets Shake Up the Tournament Heading into Week 2

Friday brought all the drama to the US Open as big names fell to unranked players and injuries changed the trajectory of the draw. It was a day of triumph for American women, with Taylor Townsend defeating fifth seed Mira Andreeva, but a solemn day for the American men as Frances Tiafoe fell to Jan-Lennard Struff after Ben Shelton was forced to retire a little over an hour earlier.
Ben Shelton Withdraws
In what was promising to be a five-set thriller, Shelton retired from his match against Adrian Mannarino after sustaining a shoulder injury at the end of the third set. The red-hot World No. 6 landed awkwardly on his left arm after running a ball down to win the third set. He called for a medical timeout in the middle of the fourth set, working his arm out with a physio on court.
It wasn't meant to be. The sixth seed attempted to remain in the set, ending points early with decisive winners at the net and rushing to hold serve on his end. However, after Mannarino won the fourth, Shelton called the match after a rundown with a trainer and a nod from his father.
It was a harsh blow to the end of the American's summer, who came into the tournament with the Toronto Masters and a quarterfinal run at Cincinnati under his belt.
"I got a lot to be grateful for," Shelton said in his post-match press conference. "Been pretty fortunate my life. Blessings, talent, a lot of things God's given me, and a small setback like this, it hurts."
No. 6 Ben Shelton retires with an apparent shoulder injury after playing four sets of his third round match at the US Open.
— ESPN (@espn) August 29, 2025
Adrian Mannarino is on to the fourth round. pic.twitter.com/8fmCQ0dsTL
Taylor Townsend Upsets Mira Andreeva
It's been one wild US Open for Townsend. After exchanging words with Jelena Ostapenko at the net following her second-round win against the Latvian, Townsend came into Friday night's match with a statement to make. Taking out the World No. 5? No problem for the American.
In just 76 minutes, Townsend dismantled an in-form Andreeva in front of a packed Arthur Ashe Stadium. Andreeve took control early in the first set, racing out to a 2-0 lead after breaking Townsend's serve.
Townsend, the current World No. 1 in the doubles ranking, stormed back to take the first set 7-5 with a massive first serve and heavy winners from the net. Andreeva fell apart after losing the first set, unable to answer most of Townsend's cross-court winners and falling to the American 6-2.
"I'm emerging as a new person," Townsend said in her post-match conference. "I feel like today I've leveled up, and I'm really just so proud of myself. I'm so proud of the way I showed up tonight, the way that I handled business, the way that I kept my head on."
Jan-Lennard Struff Upsets Frances Tiafoe
In a second stunning upset on the men's side, Tiafoe fell in straight sets to Jan-Lennard Struff. The formerly ranked World No. 21 endured three rounds of qualifiers before taking out American Mackenzie McDonald and 11th seed Holger Rune on his way to the third round.
Tiafoe was unable to meet Struff's level, struggling to make points against the big-hitting German. There was a chance at a comeback when Struff served for the match at 5-3 in the third set; however, Tiafoe quickly lost his focus.
He broke Struff and held serve to go 5-5 in the third set, and another hold from both players brought them to a tiebreak. A hard-fought 11 points later gave Tiafoe his first and only set point; however, an unforced error off his backhand led to Struff taking the next 3 points to win the match.
"I mean, I got to tip my hat to him," Tiafoe said of Struff. "He made me feel very, very uncomfortable, and I didn't do a very good job adjusting. It is what it is. I got to swallow it, but very, very tough."
Frances Tiafoe is eliminated from the US Open 😳
— ESPN (@espn) August 29, 2025
He falls in straight sets to unseeded Jan-Lennard Struff. pic.twitter.com/QMEhM1BKcv
Barbora Krejčíková Upsets Emma Navarro
In a Wimbledon third-round re-match, Emma Navarro faced off against Barbora Krejčíková on Grandstand. The tenth seed looked composed in the first set, winning 6-4 after both players traded a whopping seven breaks. The Czech dug deep to pull out a 6-4 win in the second set, but she found herself losing the opening three games of the third set.
Krejčíková took the wheel, winning the next five games for a 5-3 lead. Navarro held onto her serve to give herself a chance, but Krejčíková took the final set after serving for the match at 5-4.
"It was a huge match for me," Krejčíková said on court after her win. "I definitely enjoyed it very much. Before the last game, the crowd, the cheering, and all that, it pumped me up."
BARBORA KREJCIKOVA UPSETS NO. 10 EMMA NAVARRO 🔥
— SportsCenter (@SportsCenter) August 30, 2025
Krejcikova is a two-time grand slam winner 💪 pic.twitter.com/fxvFc2rRmg
Markéta Vondroušová Upsets Jasmine Paolini
It's been a tough Grand Slam season for Jasmine Paolini. After making two Slam finals last year, the World No. 8 has not advanced past the fourth round in any Slam this season. Paolini fell to 2023 Wimbledon champion Markéta Vondroušová 7-6 (4), 6-1 in a tense battle on Grandstand early Friday evening.
While the match was certainly no upset, given Vondroušová's past slam success and comeback on grass this past season, it was an unfortunate result for the Italian. Despite the scoreline, it was a battle to the very end, Vondroušová hitting 19 winners to Paolini's 15 with both players opting for aggressive baseline play to see who could outhit who first.
Paolini was more prone to errors, playing out a long service game while down 4-1 in the second set, but unable to seal the game due to unforced errors after unforced errors.
"It was a very important game," Vondroušová said of the game. "It's a big difference if it's 4-2 or 5-1, and it was a great game. That was the key to the match. The match overall was so fun. It was good from my side, so I'm happy to be through."
Yesterday just wasn’t my day. Reloading for tomorrow’s double match. 🇮🇹 pic.twitter.com/2kZDU8vaVS
— Jasmine Paolini (@JasminePaolini) August 30, 2025
The US Open singles tournament runs through September 7. Stay locked into Sports Illustrated's Serve On SI for all of your tennis news from the court and beyond.
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Megha Gupta is a multimedia journalist studying at Columbia University. She has a passion for exploring the intersections of fashion, culture, and sports, and previously covered the 2024 Paris Olympics at NBC Sports.
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