Roronoa Zoro is one of the strongest swordsmen in One Piece. Since his childhood, he has dreamed of becoming the best swordsman and immortalizing his name. Zoro mainly uses three swords in combat, but he can switch to one sword style or even two sword styles if the situation calls for it.

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There is no doubt that Zoro is among the very best in his field, but this wasn't always the case. In fact, Zoro has suffered multiple setbacks in his adventure. Thankfully, these failures didn't affect the swordsman mentally. Instead, they boosted Zoro's development as a fighter.

6 Failed To Do Any Significant Damage To Kaido

Let Down By His Skills At An Important Time

Kaido was the main villain of the Wano Country arc. He came to the country decades ago and forcibly took over. Under Kaido's rule, nearly the entire country was turned into a wasteland. There were armament factories everywhere, and people were left to rot in poverty. They had no hope, but when the Straw Hats arrived, they felt that they could dream again.

Fighting Kaido was never going to be an easy task. So everyone needed to be at their best. As the Worst Generation made their way to the rooftop, they were aware of what awaited them. Every member of the Worst Generation had a go at damaging Kaido, but the Yonko was almost unfazed by the majority of their attacks. Zoro also tried his luck, and he was successful to an extent. However, Kaido brushed it off and then proceeded to knock out Zoro with a single hit.

5 Underestimated Buggy

Nearly Died Because Of His Arrogance

Zoro is an arrogant individual, and he doesn't try to hide this trait. Throughout his adventure, there have been various instances where Zoro's cavalier attitude has gotten him in trouble. One of the earliest examples of this is his fight against Buggy.

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After cutting Buggy into multiple parts, Zoro thought that he had won the fight. But he had no idea that Buggy had successfully managed to avoid any damage. Due to this reason, Zoro let his guard down, allowing Buggy to wound him. The young swordsman was bleeding profusely and couldn't continue the fight in his condition, so he had to be rescued.

4 Requiring A Miracle Drug To Fight King

His Recklessness Made Him A Burden In Onigashima

The Wano Country arc was the biggest test of the strength of the Straw Hat Pirates. The crew, including Zoro, had to face extremely strong opponents, many of whom were equipped with rare Devil Fruits. After his unsuccessful attempt at trying to bring down Kaido, Zoro was left in a state of extreme fatigue. He couldn't even move on his own, so Sanji had to carry him.

Eventually, Sanji entrusted him to Chopper. The latter had to use Miyagi's miracle drug to help Zoro recover. If the medicine had not worked, Zoro would have been nothing more than a hindrance, and he would have ruined the alliance's goal of taking down Kaido and the Beasts Pirates. Luckily, Miyagi's medicine worked, and it gave Zoro the boost that he needed to fight and beat King.

3 Losing Over 2000 Times

He Lost Multiple Times To The Same Opponent

As a child, Zoro was rivals with Kuina. She was a prodigy when it came to wielding a sword. Kuina's skill with the sword was unparalleled, and it made Zoro jealous to an extent, causing him to challenge her to hundreds of duels. He lost the first one and the 2000 times after that.

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No matter what Zoro did, Kuina was a step ahead of him. Even after trying 2001 times, Zoro was unable to get the better of Kuina. He lamented over his weakness, but he was not willing to stop trying. With every duel, the respect between Zoro and Kuina grew. They even made a promise that one of them would become the strongest swordsman in the world.

2 Being Humbled By Mihawk

Failed To Even Graze Mihawk

Zoro got a taste of what it meant to be the best swordsman in the world during the Baratie arc. While the Straw Hats were busy dealing with Don Kreig's crew, Mihawk arrived at the location. Zoro recognized him right away and challenged the Shichibukai to a duel.

Given Zoro's solid reputation, fans were expecting that he would put up a good fight against Mihawk. But no one could have predicted the humiliation that Mihawk inflicted on the young swordsman. Mihawk used a small pocket knife to stop all of Zoro's attacks, and then afterward, gave him a massive wound across his torso. This was a major turning point for Zoro, as he realized that there was still a big gulf between him and Mihawk.

1 Being Defeated By The Yeti Cool Brothers

Failed To Defend Himself From The Assassins

Zoro pointed out that the crew was going to face many challenges in the New World and that they needed to be ready for everything. Unfortunately, he didn't pay much attention to his own words as he was knocked out by the Yeti Cool Brothers in Punk Hazard.

The two assassins found an opening in Zoro's defense, and they made sure to exploit it. Luckily, the Yeti Cool Brothers weren't blessed with too much power; otherwise, Zoro might not have lived to see another day. This was a particularly embarrassing moment for Zoro, and there is no doubt that he would want to erase this memory forever.

One Piece (1999)

Action

Adventure

Comedy

Fantasy

Release Date

October 20, 1999

Studio

Toei Animation

Creator

Eiichiro Oda

Streaming Service(s)

Crunchyroll , Netflix , Hulu

See at Hulu