A Look Back at the Most Stunning Upsets in the History of the US Open
The US Open has a long record of surprise results. Since the Open Era began in 1968, the tournament has seen defending champions fall in the first round, unseeded players reach finals, and heavy favorites stop just short of history.
In the matches that follow, each upset shows how quickly fortunes can turn in New York.
Vinci Ends Serena’s Calendar Slam Hopes in 2015
Image via Wikimedia Commons/Tatiana from Moscow, Russia
In 2015, Serena Williams arrived at the US Open with all four majors already secured that year. The only thing left was the final piece: winning in New York to complete the calendar-year Grand Slam. She’d done this once before with four consecutive Slam titles, but never in a single calendar year.
On the other hand, Roberta Vinci had never reached a Grand Slam singles final and was widely expected to lose quickly. Vinci played smart, kept the ball low, changed direction often, and prevented Serena from finding any balance. She took the second set, but when she won the third set 6-4, the crowd fell into silence. Serena’s bid for history ended just two matches short.
Bonzi Outlasts Medvedev in a Five-Set First-Round Battle
The 2025 tournament opened with a match that would set the tone for a chaotic draw. Daniil Medvedev, seeded 13th and a former US Open champion, took the court against Benjamin Bonzi in the first round. It wasn’t expected to be competitive. Bonzi was ranked outside the top 50 and had never gone beyond the third round at a major. But he had already beaten Medvedev that summer at Wimbledon.
The match stretched into five sets. In the third set, Medvedev erupted over a line call and argued with the chair umpire. The crowd joined in, which delayed play by several minutes. Bonzi stayed focused through the chaos. He lost the third and fourth sets but recovered in the fifth. The final score, which was 6-3, 7-5, 6-7(5), 0-6, 6-4, reflected a match filled with momentum swings. Medvedev ended the season without making it past the second round at any major, and Bonzi’s win ended up being the biggest of his career.
Coin Stuns World No. 1 Ivanovic in 2008
Image via Wikimedia Commons/Steven Pisano from Brooklyn, NY, USA
Before the 2008 US Open, few fans outside of France had heard of Julie Coin. She was ranked 188th worldwide and entered the tournament as a qualifier. Ana Ivanovic, meanwhile, was the No. 1 seed and fresh off her first Grand Slam title at Roland Garros earlier that year. The two met in the second round.
Coin came out hitting cleanly and never let the occasion shake her. Ivanovic seemed flat from the start and struggled with her serve. Coin broke early and took the first set. Though Ivanovic managed to recover in the second, she couldn’t sustain her level in the third. Coin closed it out 6-3, 4-6, 6-3. It marked the first time in 40 years that the top seed in the women’s draw had lost in the second round of the US Open.