Top 5 Most Shocking Boxing Upsets of the Last 20 Years

Boxing is full of moments that leave fans speechless. A single punch can flip the outcome; sometimes, the fighter expected to win ends up on the canvas. These surprises keep the sport thrilling from one bout to the next. We refer to these moments as boxing upsets – when an underdog rises above the odds and claims victory against a big-name opponent.

Over the last twenty years, boxing has delivered shocking results that no one saw coming. Fans still talk about these fights because of the sudden and powerful turnarounds.

Exploring 5 Memorable Boxing Upsets of the Last 20 Years

Boxing Upsets: 5. Hasim Rahman vs. Lennox Lewis (2001)

At the time of the fight, Lennox Lewis was considered nearly unbeatable. He had just defended his titles and wasn’texpected to struggle with Hasim Rahman, a lesser-known opponent with fewer big-name wins. Most fans and experts viewed the match as a warm-up for Lewis before a more significant, more marketable bout.

That idea quickly vanished in round five when Rahman threw a mighty right hand that caught Lewis off guard. The punch landed cleanly, sending Lewis crashing to the canvas in one of the most unexpected boxing upsets in heavyweight history.

Boxing is full of moments that leave fans speechless. A single punch can flip the outcome, turning an expected win into a stunning loss. These unexpected twists tap into something more profound—the thrill of unpredictability and the human love for taking risks.

This love for surprise victories and game-changing moments isn’t confined to boxing. It’s also why the popularity of online casinos continues to rise, as players worldwide seek that rush of a sudden, life-changing win. Just as a punch can instantly change a fight’s course, a single bet can flip the odds in gambling. 

Players from New Zealand and Canada—countries with established online gambling markets—have jumped on the thrill, drawn to games that pack the same punch and unpredictability as a good boxing match. Now, every online casino in New Zealand is also experiencing its boom, with more Kiwis than ever turning to digital platforms to try their luck. As with boxing upsets, New Zealand players are drawn to the idea that anyone can win, no matter their experience or how stacked the odds might seem. 

The country’s rapid growth of online casinos reflects the universal appeal of those one-in-a-million moments—the chance for a life-changing win, whether from a surprise knockout or a winning hand at the roulette table.

4. Andy Ruiz Jr. vs. Anthony Joshua (2019)

When Anthony Joshua’s original opponent dropped out, Andy Ruiz Jr. stepped in with just weeks to prepare. Most people didn’t take him seriously—he didn’t look like a typical heavyweight champ and wasn’t a household name. Expectations were low, and many saw it as an easy win for Joshua.

But Ruiz had other plans. He returned strong after getting knocked down early, showing quick hands and sharp timing. He dropped Joshua multiple times and finished the fight in the seventh round, shocking fans everywhere and becoming the first Mexican-American heavyweight champion.

The upset changed how people viewed fighters and fitness, proving that appearances don’t win fights—preparation and heart do. In the UK, where Joshua was a national icon, the loss sparked debates about focus, training, and taking challengers lightly. Ruiz’s win became a clear reminder that no belt is ever truly safe in the ring.

3. Juan Manuel Márquez vs. Manny Pacquiao IV (2012)

Few rivalries in boxing were as intense as Pacquiao versus Márquez. Their first three fights were close, but Pacquiao had won two and drawn one, leading many to believe he had Márquez figured out. As they entered their fourth match, fans expected another competitive battle, but few predicted a knockout.

During the sixth round, Márquez countered with a perfectly-timed right hand. Pacquiao fell face-first to the canvas and stayed down, sparking shock across the crowd and millions watching worldwide. It wasn’t just the win that made it a surprise—it was how it happened.

The knockout was named Knockout of the Year and had long-lasting effects. After that, Pacquiao’s future fights were viewed through a different lens, and the talk of a superfight with Floyd Mayweather cooled down for a while. For Márquez, the victory was the crowning moment of his career, turning him from a respected fighter to a boxing legend in a single second.

2. Teofimo Lopez vs. Vasiliy Lomachenko (2020)

Vasiliy Lomachenko entered the fight with a strong amateur background and titles in three weight classes. His speed, footwork, and ring IQ made him one of the top fighters in the sport. Teofimo Lopez was younger and less experienced, and many believed he wasn’t ready for someone at Lomachenko’s level.

Lopez proved the doubters wrong. He won most of the early rounds by using quick movement, solid jabs, and body shots that kept Lomachenko from finding a rhythm. Even when Lomachenko returned in the later rounds, Lopez stayed focused and held his ground.

The fight went the distance, and Lopez won by unanimous decision. It wasn’t just the win that surprised people—it was how he controlled the fight. That night showed the new generation of fighters was ready to take over.

1. Eleider Álvarez vs. Sergey Kovalev (2018)

Sergey Kovalev was known for his punching power and had regained the WBO light heavyweight title. Many expected him to beat Eleider Álvarez, who had been waiting for his title shot for a long time but hadn’t yet faced a challenge on Kovalev’s level. Most of the early rounds followed the script, with Kovalev building a slight lead on the scorecards.

In round seven, everything changed. Álvarez found the opening he needed and dropped Kovalev with a sharp right. He followed up with two more knockdowns, forcing the referee to stop the fight and hand him a dramatic TKO win.

This fight proved that even experienced champions can be surprised. Álvarez’s patience and calm under pressure paid off massively. His win reshaped the light heavyweight division and added his name to the list of fighters who shocked the world.

Even though Álvarez didn’t hold the title for long, that moment stands out as proof that timing, preparation, and belief can break any expectation.

Final Thoughts

Boxing’s biggest surprises are often its most memorable moments. They show us that no matter the odds, any fighter can rise to the occasion and change everything with one punch. That keeps fans hooked—the thrill of not knowing how a fight will end. These boxing upsets don’t just rewrite scorecards; they write history, reminding us that anything can happen in boxing.