US Open: The 9 biggest upsets in tournament history – ranked!

Pictured: Leylah Fernandez and Roberta Vinci at the US Open
Leylah Fernandez and Roberta Vinci star in our nine biggest US Open upsets.

The US Open has played host to many memorable matches and, in particular, some of the most epic upsets in tennis history.

With the 2024 tournament now underway, we rank nine of the biggest upsets in US Open history.

9) Marin Cilic def Roger Federer, 2014 SF

After Kei Nishikori had shocked Novak Djokovic in the first semi-final, Federer became the overwhelming favourite to lift what would have been a sixth US Open crown.

The Swiss was in resurgent form throughout 2014 and had a commanding 5-0 lead against Cilic in their head-to-head, with the Croatian in just his second Grand Slam semi-final.

However Cilic had other ideas and, in arguably the best performance of his career, cruised past Federer in an emphatic 6-3, 6-4, 6-4 victory.

The 14th seed went on to lift the title, and that remained his only victory against Federer – losing their next five matches.

8) Ekaterina Bychkova def Svetlana Kuznetsova, 2005 Round 1

Former world No 2 Kuznetsova became the first defending US Open women’s champion in history to lose in the opening match of her title defence, falling to compatriot Bychkova in straight sets.

Kuznetsova had stormed to the title as a 19-year-old in 2004 and, despite a lingering back injury, the fifth seed was still a heavy favourite for her opening match the following year.

Bychkova ranked 97th in the world and had never played a Grand Slam main draw match before this, but shocked the tennis world with a staggering 6-3, 6-2 triumph.

She fell in the next round and achieved a career-high ranking of 66th in 2006.

7) Leylah Fernandez def Naomi Osaka, 2021 Round 3

The reigning US Open and Australian Open champion, third seed Osaka was a leading contender to claim a third title at Flushing Meadows in 2021.

After receiving a walkover in round two she was a significant favourite against the unheralded Leylah Fernandez in the third round, with the world No 74 making just her second US Open appearance.

Osaka served for the match in the second set but was unable to close it out and, after forcing a decider, Fernandez claimed a seismic 5-7, 7-6(2), 6-4 victory.

She would then go on to beat Angelique Kerber, Elina Svitolina, and Aryna Sabalenka to reach the final.

6) Bill Scanlon def John McEnroe, 1983 Round 4

World No 1 McEnroe was a leading contender to regain his US Open title in 1983, having won the tournament three years in a row from 1979 to 1981.

The American progressed to the second week where he found himself the heavy favourite against 16th seed Bill Scanlon, who had reached just two Grand Slam quarter-finalists previously.

But Scanlon picked up the first two sets in tiebreaks and, after dropping the third set, rallied to seal a 7-6(2), 7-6(2), 4-6, 6-3 triumph and progress to the last eight.

He went on to reach the sole major semi-final of his career, while it snapped a streak of five consecutive US Open semi-finals for McEnroe – though he recaptured the title in 1984.

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5) Julie Coin def Ana Ivanovic, 2008 Round 2

World No 188 Coin is one of the lowest-ranked players in history to defeat a reigning world No 1 thanks to her shock win over Ivanovic 16 years ago.

Ivanovic had not been at her best since her French Open triumph earlier in the season but was still a significant title contender in New York, and was highly-fancied against qualifier Coin in round two.

But the Frenchwoman held her nerve to close out the upset, beating the Serbian 6-3, 4-6, 6-3 in front of a stunned Arthur Ashe Stadium.

It was the only time Coin reached the third round of a major, and she achieved a career-high ranking of 60th in 2009.

4) Jaime Yzaga def Pete Sampras, 1994 Round 4

Sampras’s haul of five US Open titles is a joint record for the men’s singles, and the American came into the tournament 30 years ago attempting to defend the second title he had won in 1993.

The top seed dropped just one set on his way to the second week and was an overwhelming favourite against Peru’s Jaime Yzaga, who had beaten 1993 runner-up Cedric Pioline in the third round.

The world No 23 found himself two sets to one down but was undeterred and battled back to seal an epic five-set triumph, prevailing 3-6, 6-3, 4-6, 7-6(4), 7-5 to reach his first US Open quarter-final.

Yzaga reached a career-high of 18th and won eight ATP titles – though was beaten convincingly by Sampras in the second round a year later.

3) Arnaud Clement def Andre Agassi, 2000 Round 2

A year on from his second US Open triumph in 1999, Agassi returned in 2000 as the top seed.

The US star cruised through his opener and was a significant favourite for his second round match against Clement, even if the Frenchman had pushed him to five sets at the 1999 French Open.

However, the world No 37 had other sides and dominated this match from start to finish, breezing towards a surprisingly easy 6-3, 6-2, 6-4 win.

Clement would go on to reach the last eight and then the final of the 2001 Australian Open – where he lost to Agassi in straight sets.

2) Alexander Volkov def Stefan Edberg, 1990 Round 1

Having just won his second Wimbledon title and risen to world No 1 for the first time, Edberg entered the US Open on a 21-match win streak – and was the favourite for the title.

But the Swede had already suffered a shock opening round loss at the French Open earlier in the year, and this time fell to Volkov in one of the biggest upsets in US Open history.

In a fearless performance, Soviet star Volkov stunned the world No 1 6-3, 7-6(3), 6-2 for the most significant victory of his career.

The world No 52 lost his next match but went on to reach the last four in 1993 and reach world No 14 in the ATP Rankings.

1) Roberta Vinci def Serena Williams, 2015 SF

In 2015, the stage was set for Williams to write an extraordinary chapter of tennis history – only for Vinci to stun the sporting world in one of the biggest shocks of all time.

Williams was the three-time defending US Open champion, and the last four Grand Slam events to complete a second ‘Serena Slam’ – and was going for her first Calendar Grand Slam.

The American stormed through the draw and was the overwhelming favourite to beat world No 43 Vinci, who was in her first major singles semi-final.

But, despite dropping the opening set, the Italian bamboozled Williams and triumphed 2-6, 6-4, 6-4 in a performance that will never be forgotten.

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