Defying the Odds: Memorable Upsets in US Open Tennis History

The US Open has witnessed numerous exhilarating moments over the years, with upsets being an integral part of its storied history. These are the matches where underdogs defy the odds, defeating higher-ranked opponents and leaving a lasting impact on fans and the tennis world. From unexpected defeats of legendary players to rising stars making their mark, memorable upsets at the US Open have provided some of the tournament’s most compelling narratives. Discover more about the US Open Memorable Upsets.

In this article, we will delve into seven of the most unforgettable upsets in US Open history, each of which has left an indelible mark on the annals of tennis.

Jimmy Connors vs Aaron Krickstein 1991:

In the fourth round of the 1991 US Open, 39-year-old Jimmy Connors faced off against 24-year-old Aaron Krickstein in an epic encounter.

Connors, the crowd favorite, fought back from two sets down and saved several match points to secure a dramatic five-set victory. This thrilling upset displayed Connors’ never-say-die spirit and became one of the most memorable moments in US Open history, leaving fans in awe of his ageless determination.

Pete Sampras vs Richard Krajicek 1996:

In the quarterfinals of the 1996 US Open, defending champion Pete Sampras encountered an inspired Richard Krajicek.

The Dutchman’s powerful serve and precision groundstrokes proved too much for Sampras, who fell in straight sets. This stunning upset ended Sampras’ quest for a fifth consecutive US Open title and showcased the threat posed by big-serving players on the fast Flushing Meadows courts.

Serena Williams vs Roberta Vinci 2015:

In a highly anticipated 2015 US Open semifinal, Serena Williams, gunning for the calendar-year Grand Slam, faced unseeded Italian Roberta Vinci.


In one of the biggest upsets in tennis history, Vinci’s crafty game and clever shot-making halted Williams’ historic run. Vinci’s 2-6, 6-4, 6-4 victory denied Serena the chance to achieve the elusive calendar-year Slam, and the Italian’s jubilant celebration will forever be etched in US Open lore.

Andre Agassi vs Benjamin Becker2006:

The 2006 US Open marked the final Grand Slam appearance of tennis icon Andre Agassi. In the third round, Agassi faced unheralded German qualifier Benjamin Becker. Despite battling severe back pain, Agassi put on a valiant display, winning the first two sets.


However, Becker’s relentless determination and powerful serves saw him stage an astonishing comeback to eliminate the American legend. The emotional defeat marked the end of Agassi’s illustrious career on the Grand Slam stage.

Martina Hingis vs Kimberly Po-Messerli 1998:

In 1998, the reigning world No. 1 and top seed Martina Hingis entered the US Open as the favorite to lift the title. However, her journey was halted in the opening round by American qualifier Kimberly Po-Messerli. Po-Messerli’s aggressive play and impressive net skills stunned Hingis, leading to a straight-sets victory for the underdog.


The upset sent shockwaves through the tennis world and proved that anything can happen in the pressure-cooker environment of Grand Slam tennis.

Novak Djokovic vs Stan Wawrinka 2014:

In the 2014 US Open quarterfinals, world No. 1 Novak Djokovic faced the formidable Swiss Stan Wawrinka. Despite Djokovic’s dominance that year, Wawrinka unleashed his powerful backhand and demonstrated impeccable shot-making to outclass the Serbian in four sets.


This victory not only ended Djokovic’s quest for the Calendar Year Grand Slam but also highlighted Wawrinka’s emergence as a force to be reckoned with on the biggest stages of tennis.

Suggested Read: The US Open Winners: Celebrating the Champions!

Wrapping It Up

Memorable upsets at the US Open have provided some of the tournament’s most gripping and unforgettable moments. From veterans defying age to underdogs overcoming insurmountable odds, these upsets showcase the essence of sports – unpredictability and determination. Each of the highlighted matches holds a special place in tennis history, etching the names of these unheralded victors in the annals of the sport. As the US Open continues to captivate audiences worldwide, the potential for more astonishing upsets looms, ensuring that the magic of this prestigious tournament lives on for generations to come.

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Waleed is a dedicated journalist who is always looking for the truth. He has a knack for weaving complicated tales. Waleed always manages to focus in on the core of any issue, whether it's political or human interest. Waleed maintains his fresh and inventive spirit through sports and video games. Waleed is a leading figure in his field, known for his ability to influence others through his regular sharing of useful information.

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