Zoro relentlessly pursues to be stronger than Kuina and fights her 2000 times, but not once being able to defeat her. After that, he tells her about his dream of becoming the world's best swordsman.
Mihawk– Zoro faced Mihawk in Baratie Arc. In order to become the greatest swordsman, he challenged the current title holder. Despite his unique three sword style technique he still suffered a crushing defeat.
9 Zoro Vs.
Roronoa Zoro's biggest goal at one point was defeating Kuina and surpassing her in combat. In total, he challenged her 2001 times and lost every single battle. After her death, Zoro promised to become the best swordsman in the world and to keep the promise he made to her.
Zoro, who is used to being chill, never thinks about the path he will take when he wants to get to his destination. This is one of the reasons why he often gets lost. Zoro is more often annoyed and acts as he pleases until he always ends up getting lost.
In his first appearance, Mihawk humiliated and almost killed the Straw Hats' Zoro, who also dreams of becoming the world's strongest swordsman. After that defeat, Zoro swore of defeating Mihawk, but he actually ended up training with him during the "two-year gap".
Mihawk is said to be close to the same level as Shanks and is even dubbed as the greatest swordsman, so to say Luffy would defeat Mihawk is still debatable in the eyes of many fans.
Luffy is close to Shanks in terms of power and it is only after their fight that he will officially be able to call himself stronger than Shanks.
In it, Zoro, while anxious to advance after showing progress in his training, is quickly humbled by his teacher, resulting in the loss of his eye. While it may not be canon, it certainly is believable, especially considering the two personalities involved.
Yes, Zoro has a fear of stampeding naked men.
It's entirely possible Mihawk noticed through their duel and training that Zoro suffers from ocular dominance in his left eye. That is to say, the left eye is stronger than the right. As a result, maybe Mihawk scarred the left eye shut and instructed Zoro not to open it until his right eye was trained enough.
1 Luffy Vs.
The fight is, undoubtedly, the most difficult one that Luffy has fought so far. Kaido managed to defeat Luffy three times. For the first time, Luffy faced defeat against him Kuri and was thrown in prison.
Quite easily one of the toughest battles that Zoro has been in is the one that he fought against Dracule Mihawk, the man who currently holds the title of the World's Strongest Swordsman. Zoro challenged him during the Baratie arc and found out the gulf of power between him and the World's Strongest Swordsman.
He faced off many opponents. Some he defeated after major efforts, while others overpowered him. Here are five times Sanji came out victorious in a fight, and five times he suffered a humiliating defeat.
Dracule Mihawk is Zoro`s greatest rival and holds the title of the strongest swordsman in the world. Mihawk is extremely skilled with the blade and his sword fighting is described as very aesthetic. He is also extremely good at using Haki as he taught Zoro how to use it.
That said, there is one crew member who stands above the rest in terms of loyalty to Luffy: Roronoa Zoro. The Straw Pirates' first mate has proven his loyalty on numerous occasions throughout the series, even putting his crew mates' well-being above his own life.
Zoro Vs Killer
The fight in general was well animated with a rigorous clash between these two pirates. Despite Zoro suffering a pretty serious injury (when does he not?) from Killer, he was able to get the upper hand on Killer by using his scythe to defeat him.
Zoro x Hiyori
The Wanokuni arc of One Piece gave Zoro the spotlight he deserved but fans were more gravitated toward his scenes with Hiyori. It wouldn't surprise fans if Hiyori reveals her feelings for Zoro, her savior. They shared intimate moments and Zoro might even find a sense of belongingness when he's with her.
Hiyori and Zoro proceeded to talk about the current status of the alliance including the whereabouts of each of the Nine Red Scabbards. After their conversation, Hiyori wondered if she should meet her brother. Hiyori and Toko then slept with Zoro and later woke up to meet Brook.
20 Zoro x Perona
Their relationship only improved further during the timeskip, as she risked her own safety to help escort Zoro to the Sabaody Archipelago and helped him and the Straw Hats escape the Marine ambush that happened shortly after.
During this arc, Zoro and Luffy, having lost their memories, confront each other and engage in a fight. It is during this fight that Zoro lands a strong surprise attack on Luffy, slicing his chest and thus giving him the X-shaped scar.
Nope. Because he has the sharingan. Kidding, After the two-year timeskip, Zoro gains a new scar running down his left eye, which is now implied to be critically injured as it is always closed.
The concept of power up Gears has been a core part of the One Piece franchise and allowed Luffy to take on the most difficult of foes. Fans speculate Gear 6 is inevitable – and with the series winding up to its conclusion, it could play a pivotal part in the final conflict.
With its powers, Luffy was able to topple even Kaido and if he could defeat the man who was the Strongest Creature Alive, he can certainly defeat Shanks as well.