Top 10 moments in US Open Tennis history—iconic wins & shocks

The most prestigious events in tennis are the Grand Slams, and the US Open Tennis Championship has a special place in them. Every year, this event creates moments that endure for centuries. Be it an emotional victory or a battle of rivalries, the US Open has always inspired fans.

A collage of iconic US Open tennis moments featuring Serena Williams, Roger Federer, Pete Sampras, Naomi Osaka, and Arthur Ashe Stadium backdrop
US Open historic moments

In today's blog post, we are going to talk about such top 10 moments in US Open tennis history. This post is for all those who are already tennis fans and those who have just started watching the Grand Slam.


Overview Table of Top 10 US Open Tennis Moments

Rank

Moment

Year

Players Involved

1

Serena's First Slam Win

1999

Serena Williams vs Hingis

2

Federer vs Agassi Epic

2004

Federer vs Agassi

3

Monica Seles’ Comeback

1995

Seles vs Maleeva

4

Andy Roddick's Title

2003

Roddick vs Ferrero

5

Naomi Osaka Beats Serena

2018

Osaka vs Serena

6

Sampras Retires as Champion

2002

Sampras vs Agassi

7

Djokovic’s Grand Slam Drama

2021

Djokovic vs Medvedev

8

Connors at 39

1991

Connors vs Krickstein

9

Venus Breaks Barriers

2000

Venus Williams’ Title

10

Del Potro’s Shocker

2009

Del Potro vs Federer

Detailed elaboration of all top 10 moments in US Open tennis history

🎾 Moment #1: Serena Williams’ First Grand Slam (1999)

Serena Williams, who is considered to be the most legendary tennis player, retired from the Grand Slam in 2023. She was just 17 years old rookie when she played her debut Grand Slam in 1999. For the first time on such a big stage, she defeated Martina Hingis and won her first Grand Slam. An experienced player who ruled tennis in the 1990s, won 3 Grand Slam titles in 1997, and was defeated by Serena in her debut.

This victory was a cultural and generational shift in the tennis world. With this victory, Serena Williams created history to become the first African-American woman tennis player to win the Grand Slam US Open. She achieved this victory with a final score of a 6–3, 7–6.

What was special about this moment?

  • It was the biggest win of Serena's career and the first ever Grand Slam title.
  • Despite being a young player, she beat a player who had already won five Grand Slams. With this she proved that even young, rookie players can handle any situation and pressure.
  • The US Open 1999 was a top moment where fans got their first young star, and Serena's legendary career also started.

🎾 Moment #2: Federer vs. Agassi—Generational Clash (2004)

This was one such moment, which is still included in the history of the US Open. In the quarterfinals of the US Open in 2004, players from two different generations faced each other. One player was the legendary Andre Agassi, who had won a total of 8 Grand Slams in his entire career and had also been the world No. 1 tennis player many times in the 1990s. The other competitor was the emerging tennis sensation of that period, Roger Federer.

Both these players are also known for their playing styles and techniques. In this match, not two different players but two different generations and playing styles clashed. Agassi gave his all and played aggressively, and Federer won this match with his calm and class. This victory was quite unpredictable, but Federer won over the fans.

In a way, the encounter was also a generation shift match, which was like the entry of new rising stars into a new tennis era. This was a battle of respect, legacy, and transition.

What was special about this moment?

  • On one side there was an experienced player, and on the other side there was a rising star.
  • This was a signal that the generation is shifting from old legends to new kings.
  • The match was very interesting; Roger maintained control over it from the beginning. Its score (6–3, 2–6, 7–5, 6–3) shocked all the fans. But the thrill of this match made this moment immortal forever.

🎾 Moment #3: Monica Seles' heart-touching comeback (1995)

In 1993, the most horrific incident in the history of tennis was when an obsessed fan stabbed Monica Seles on the court during a match, leaving her badly injured. After this incident, she took a break from tennis for a year and a half. All her fans and admirers thought that she would never return to playing tennis again. But this did not happen; rather, Monica Seles returned to the field in the 1995 US Open tennis tournament with full courage and enthusiasm. Her comeback was very emotional, which made everyone cry at that time. But as soon as Monica entered the court, the entire crowd welcomed her with a standing ovation and saluted her courage and spirit from the heart.

In this emotional comeback, Monica put in all her strength, and she also reached the finals of the US Open. In the finals, she faced the legendary Steffi Graf and unfortunately she lost that match. But no one was saddened by her loss because everyone had realized Monica's ability to recover from difficult times. Fans were thrilled that she performed at such a level even after such a big tragedy and accident.

The result is still considered the most emotional comeback in the history of the US Open. It reflects true sportsmanship.

What was special about this moment?

  • The most remarkable aspect of this moment was the passion. Even after such a big loss, Monica made herself capable enough to reach the finals of the most significant tennis tournaments in the world.
  • Monica demonstrated that courage is not only essential on the court, but also in everyday life.
  • Her comeback story influences every person who is going through a difficult time but still wants to do something to move forward.

🎾 Moment #4: Andy Roddick’s Only Slam (2003)

In 2003, the world was close to getting a rising star. In 2003, the US Open gave birth to a new star, Andy Roddick. At the age of 21, he was already reaching the heights of his career. He had the strength of a 140+ mph explosive serve and killer confidence. In 2003, when he entered the field for his first Grand Slam, the US Open, he was facing Spain's Juan Carlos Ferrero. This match was very intriguing, and Andy Roddick won his first and last Grand Slam in it.

This was Andy's first and last title because next year i.e in 2004, Roger Federer entered tennis, and the game changed totally. Roger Federer never permitted Roddick to win the title. Roger Federer, followed by Rafael Nadal and then Novak Djokovic, dominated the sport to the extent that no other players were able to win the title during their reign. And Andy Roddick became the victim of this. It was not that he did not play after this; he played in the 2004 Wimbledon finals but lost to Federer. After that, he reached the finals in 2005, and Federer defeated him again. In the 2009 Wimbledon finals, he faced a tough battle but ultimately lost in the final set. After this, he retired in 2012.

This emotional moment from the US open remains unforgettable for every fan of that era. Because when Roddick won his first Grand Slam, everyone felt that now a new rising star had arrived, but it remained his first and last title.

What was special about this moment?

  • Roddick's win in 2003 was not just a victory but the beginning of a new era for US tennis.
  • Roddick's serving was very fast and powerful, which impressed the youths a lot.
  • Fans still wish Roddick had won more Grand Slams.

🎾 Moment #5: Naomi Osaka Beats Serena in a Historic and Controversial Final (2018)

This moment of 2018 was very much in discussion at that time. It so happened that the final match of the US Open tennis tournament had started in 2018. On one side was Serena Williams, who had won the Grand Slam title 24 times, and on the other side was a Japanese debut player, Naomi Osaka, for whom the moment was her first Grand Slam final. At that moment, the crowd was confident that players like Serena would easily defeat a young player, but to their surprise, Serena lost decisively.

Actually, when the match started, Serena was given a code violation due to some arguments from the umpire. Due to this, she lost her focus a bit, although the whole crowd was with her and was also cheering in her support. Due to this pressure, she could not focus properly. But amidst all this controversy and even in such a tense atmosphere, Naomi Osaka did not let her focus shift even a bit, and as a result, she secured her first Grand Slam title with a groundbreaking score against Serena 6–2, 6–4.

What was special about this moment?

  • Naomi showed calm and maturity under pressure and kept her focus on the game.
  • Naomi defeated the world no. 1 player, but she remained humble and grounded.
  • This moment was memorable because a young player showed her strength even in a tough situation.

🎾 Moment #6: Pete Sampras Retires with a Win (2002)

In the 2002 US Open men's singles, there was a match between two players in the finals. One of them was Pete Sampras, who had won the Grand Slam 13 times, and on the other side was his biggest rival, Andre Agassi. Now everyone thought that Agassi would win this match, because Pete Sampras's game had been going down for the last few years; it had been a long time since he won the last Grand Slams, and he had not won any new titles till now. As a result, people began to believe that Sampras no longer possessed the strength he once had.

But in the middle of all this, Pete Sampras gave such a big surprise to the people that even today it is considered the most unique and best surprise ever in the tennis world. In this match, he defeated his longtime rival player Andre Agassi with a score of 6–3, 6–4, 5–7, 6–4, which became a very emotional and iconic moment. This was his 14th Grand Slam title. 

This victory is considered the most iconic in history because it was a perfect career farewell. It is a wonderful thing for a player to retire with such a victory and not with a defeat. And that is what happened; Pete Sampras gave the world's most unique farewell to tennis.

What was special about this moment?

  • Pete Sampras achieved an iconic victory in his final match before retirement, following years of defeats.
  • This was the only farewell in which there was no grand party, no drama, just a champion bidding adieu to the game with an iconic win.
  • By defeating his rival, he set the strongest theme of his career.
  • This was the title of most Grand Slam wins till that time, until Federer broke it.

🎾 Moment #7: Djokovic's Denial of the Calendar Slam (2021)

In 2021, another memorable moment occurred. Actually, in 2021 Novak Djokovic had won 3 out of 4 tournaments of Grand Slams, i.e., the Australian Open, French Open, and Wimbledon. Only the US Open was left to be won, by which he would have become the first player in the world after 1969 to have completed the Calendar Slam.

However, many believed that Novak Djokovic would win these tournaments as well; he started strong, but in the finals, he faced Daniil Medvedev, who defeated him in straight sets (6–4, 6–4, 6–4).

This was a very emotional moment, because only Rod Laver had achieved this achievement in 1969; after that, no one was able to make a record of this level. Novak Djokovic was very close to breaking that record, but one match shattered his dream.

Even after this emotional breakout, the crowd fully supported Novak Djokovic and kept cheering for him. This moment was very emotional because at that time Novak sat on the bench and cried. Seeing this, every fan's eyes were filled with tears. In his interview, Novak reflected, "Today I realize that the people who love me do not do so solely because of my profession; they appreciate me as a person." I also matter a lot to them as a person.

What was special about this moment?

  • Despite so much pressure, Novak maintained his dignity.
  • This was the biggest win of Medvedev's life.
  • Djokovic showed that just winning is not enough, but handling defeat is just as important.

🎾 Moment #8: Connors’ 1991 Quarterfinal Run at 39

Jimmy Connors, who had won 8 Grand Slams and 5 US Opens, in 1991, at the age of 39, did something that no one had even expected. In tennis, age is a significant factor, leading many to believe that Jimmy no longer had the energy to compete, especially with the emergence of four new players and a wave of rising stars.

In 1991, he faced Aaron Krickstein in the 4th round. The match went to 5 sets, and such tension had been created that it seemed that Connors would not be able to handle it, but he made an epic comeback. He fought on every point and kept making the cheers of the crowd his strength. When the momentum came in his favor, the crowd became more energetic. Then in the middle of the match, looking towards the camera, Connors passed a “statement—"This is what they paid for!” This quote and the way he delivered it became so popular that it is still considered the most iconic quote in tennis history.

In 1991, at the age of 39, he reached the quarterfinals. This was nothing less than a miracle.

What was special about this moment?

  • This was like an emotionally charged throwback for tennis.
  • Connors proved that age is just a number for a sportsman. If a person has passion, he can do anything.
  • This match became very popular in the 90s; especially his dialogue became very famous.

🎾 Moment #9: Venus Williams carries forward the legacy (2000).

In 1999, Serena Williams won her first Grand Slam by winning the US Open, making her the first African-American woman to win the title. The previous champion was Althea Gibson. Serena's elder sister, Venus Williams, is also a talented tennis player who followed in her sister's path by winning her first Grand Slam title, Wimbledon, in 2000 and then the US Open title as well. The two sisters were the first sister duo to achieve this feat.

What was special about this moment?

  • Venus demonstrated that she could achieve any goal with power, elegance, and determination.
  • Today, we see the legacy of players like Serena and Coco Gauff, and Venus is a part of that.

🎾 Moment #10: Del Potro’s Upset Over Federer (2009)

Juan Martín del Potro defeated Roger Federer in an epic five-set classic in the US Open finals of 2009. The win shocked many people, as it was a time when Federer was a dominant player and in outstanding form. No one expected such a defeat. But Del Potro kept his composure and won his first Grand Slam title.

What was special about this moment?

  • Federer had already won the US Open in five seasons, and this was his sixth title, which everyone expected him to win.
  • When Juan Martín del Potro defeated Federer, he was only 20 years old and had no experience of Grand Slams, yet he defeated the defending champion in his debut match.
  • The match was five sets; in the beginning, the game was in the hands of Federer, but del Potro soon made a comeback.

Conclusion

So these were some of the top 10 moments in US Open tennis history. In which many new players defeated the defending champions in their debut matches, while some won with their calmness even in tough situations. And some had such high spirits that they completed the journey to the finals even after injury. Some brought the first title for their country, while some missed the biggest goal of their life. We have told you about many such unique moments in today's blog post. The US Open 2025 season is going to start soon. So start preparing without delay; if you want to watch it live, then book tickets, and if you want to watch it from home, then take a subscription today itself.


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