The Most Memorable Upsets in Grand Slam Tennis History

21 October 2025

There’s something about an underdog tale that just grabs your heart, right? In tennis, where superstars like Roger Federer, Serena Williams, and Novak Djokovic have dominated for years, it’s those jaw-dropping moments—the upsets—that we live for. You know the ones. When the crowd gasps. When the commentators can’t believe what they’re watching. And when a relatively unknown player swings for glory and connects big time.

Grand Slam tournaments—the Australian Open, French Open, Wimbledon, and US Open—are like the Hollywood stage of tennis. It’s where reputations are made or broken, and where dreams either soar or crash into the net. Over the years, we’ve witnessed some truly unforgettable upsets that turned the tennis world upside-down.

So, grab your favorite snack, sit back, and let’s walk down memory lane, revisiting the most memorable upsets in Grand Slam tennis history that left fans stunned and glory rewritten.

What Makes an Upset So Special?

Before we dive into the list, let’s take a second to talk about why upsets hit differently in tennis. This sport is brutally honest—just you, your opponent, and the racket. No teammates to rely on. No timeouts. No do-overs.

When rankings and reputations take a backseat to grit, hustle, and pure guts, magic happens. That’s what makes these upsets so memorable. They're not just about numbers—they're about heart.

1. Emma Raducanu Wins the 2021 US Open as a Qualifier

Let’s be real: nobody—and I mean nobody—saw this coming.

Emma Raducanu, an 18-year-old British qualifier ranked 150th in the world, didn’t just win a few matches at the 2021 US Open. She won the whole dang tournament—without dropping a single set. Let that sink in.

She started in the qualifying rounds, meaning she had to win three matches just to enter the main draw. Then she steamrolled through seasoned pros like Belinda Bencic and Maria Sakkari, before taking down Canadian teen Leylah Fernandez in the final.

What was so magical about Emma’s run? It was fearless. She played like the moment belonged to her. And the crowds loved every second of it.

2. Goran Ivanišević’s Wildcard Wimbledon Victory in 2001

Goran Ivanišević was a name tennis fans knew well. He had reached three Wimbledon finals in the '90s but had never lifted the trophy. By 2001, the Croatian was ranked 125th in the world and received a wildcard entry into Wimbledon—kind of like tennis’ version of a Hail Mary.

And boy, did he make it count.

Ivanišević battled past some of the sport’s heaviest hitters, including Carlos Moyá, Marat Safin, and Tim Henman, en route to the final. In a five-set thriller against Aussie Patrick Rafter and with a crowd full of nerves and cheers, Goran did the unthinkable and finally took home the championship.

His victory was more than an upset—it was a feel-good sports movie playing out in real life.

3. Roberta Vinci Knocks Out Serena Williams – US Open 2015

Serena Williams was just two matches away from achieving the Grand Slam (winning all four majors in a calendar year) in 2015. Everyone—fans, analysts, even her opponents—was convinced she’d pull it off.

Enter Roberta Vinci.

The unseeded Italian, known more for her doubles play, stunned the world by defeating Serena in the semi-finals. Nobody had given her a chance. She hadn’t even made it past the quarterfinals of a Grand Slam before.

But Vinci played the match of her life, slicing and dicing with variety and confidence. After the win, she could barely believe it herself. She smiled, apologized to the crowd for spoiling the “Serena Slam,” and joked, “I tried to enjoy it.” Absolute legend.

4. Sloane Stephens Dazzles at the 2017 US Open

Talk about coming back from the brink.

Just months before the 2017 US Open, Sloane Stephens was ranked outside the Top 900 after undergoing foot surgery. Fans were happy just to see her back on the court. But Stephens? She had other plans.

Match after match, Stephens gained momentum. Her fluid play and fiery court presence lit up Arthur Ashe Stadium. In the final, she dismantled her good friend Madison Keys in straight sets.

Her fairytale comeback reminded everyone that rankings are just numbers and resilience is everything.

5. Stefan Edberg Falls to Michael Chang – French Open 1989

Picture this: a 17-year-old American taking on the world No. 3 in the final of the French Open. And not just any 17-year-old—Michael Chang.

Chang had already made headlines by beating then-world No. 1 Ivan Lendl in the fourth round after cramping and resorting to underhand serves. Talk about gutsy!

In the final, he took down Stefan Edberg in five sets, becoming the youngest male Grand Slam champion in history. His speed, grit, and never-say-die attitude captured the hearts of tennis lovers everywhere.

6. Lleyton Hewitt Falls to Ivo Karlović – Wimbledon 2003

This one? Total shocker.

Lleyton Hewitt was the defending Wimbledon champion and world No. 1. Ivo Karlović? A 6-foot-10 Croatian playing in his very first Grand Slam match.

In what felt like a real-life David vs. Goliath role reversal, Karlović’s booming serve and surprising touch around the net stunned Hewitt in the very first round.

Fans were left scratching their heads. Who was this guy? And was this the craziest first-round exit ever? Spoiler: it just might be.

7. Venus Williams Takes a Fall at Wimbledon 2014 – Defeated by Kyrgyzstan’s Larcher de Brito

Venus Williams is Wimbledon royalty. She’s won multiple titles on the grass courts of London and has always been a fan favorite.

So when little-known Michelle Larcher de Brito—a player from Kyrgyzstan ranked outside the top 100—beat her in the 2014 second round, jaws hit the floor.

Sure, Venus wasn’t at her peak that year, but few expected such an early exit. It was one of those matches where the underdog played with a kind of abandon, leaving nothing behind. And that’s what makes tennis so thrilling.

8. Naomi Osaka Gets Upset by Coco Gauff – Australian Open 2020

Coco Gauff burst onto the tennis scene at just 15 years old with fearless play and an infectious energy. In the 2020 Australian Open, she faced defending champion Naomi Osaka in the third round.

Most expected Osaka to cruise through. But Coco had other ideas.

Blazing through rallies and using her quick feet and tennis IQ beyond her years, Gauff scored a straight-sets win. It wasn’t just an upset—it was a statement.

This young star wasn’t just here to participate. She came to win.

9. Novak Djokovic Stunned by Denis Istomin – Australian Open 2017

Let’s not forget this one.

Novak Djokovic had won the Australian Open six times and was the defending champ in 2017. Denis Istomin, a wild card from Uzbekistan ranked outside the top 100, wasn’t supposed to pose any threat.

But five sets and nearly five hours later, Istomin walked off the court victorious, having conquered one of the game’s greats. It was Djokovic's earliest exit in Melbourne in over a decade and shocked the entire tennis world.

What These Upsets Teach Us

There’s a reason sports fans hold these matches close to their hearts. These upsets teach us that:

- Every match matters.
- Rankings aren’t everything.
- The human spirit is unpredictable, powerful, and often underestimated.

They remind us that in life—just like in tennis—anything can happen. When preparation meets opportunity, even the unlikeliest contender can shine on center stage.

Why We Love the Underdogs

Let’s be honest. We love seeing destiny rewritten. Seeing someone seize their one shot and turn it into legend? That’s the stuff we live for.

Whether it’s a teenager who’s never been on the main stage or a veteran making one last run, these moments show us that greatness isn’t just for the chosen few. Sometimes, it’s just waiting to be grabbed—one swing of the racket at a time.

Final Serve

Tennis might be a game of skill, strategy, and stamina. But what really keeps us coming back? The surprises. The upsets. The moments when the world pauses, jaws drop, and a new name is etched into history.

So next time you’re watching a Grand Slam and the underdog is down a set or two? Don’t change the channel. Because a tennis upset isn’t just a win—it’s a memory in the making.