Itachi Uchiha is often regarded as one of the most beloved antiheroes of the Naruto universe. Although he made his debut as a sinister, clan-murdering villain in service to the mysterious Akatsuki, his secret motives were explored and his actions were justified shortly after his death at his brother's hands.
Throughout the series, Itachi has had many opportunities to prove his martial prowess, and he did not disappoint. By identifying his best fights and their outcomes, we can better understand what makes him the most talented genjutsu user of the Five Nations and the many ways he has single-handedly influenced the story.
10 Itachi & Kisame Infiltrated The Leaf Village To Hunt Naruto
As members of the Akatsuki, Kisame and Itachi were given the responsibility of finding and capturing the Nine-Tails jinchuriki. Pain anticipated that Itachi would be best suited for the job, given his previous role as a member of the Anbu black ops.
Despite the villains' subtle disguises, they were quickly discovered and apprehended by Konoha's vigilant jonin. Although their cover was blown, the evildoers had no intention of surrendering or leaving quietly.
9 WINNER: The Jonin Successfully Forced The Akatsuki To Retreat
At first, Kisame and Itachi were confident about their odds of victory. Against Asuma, Kakashi, and Kurenai, they had a reasonably high chance of success.
However, the commotion of the battle drew the attention of taijutsu genius Might Guy. Since he was capable of fighting opponents without making eye contact and didn't use chakra that Samehada could devour, he countered both enemies perfectly. Realizing that more reinforcements would arrive the longer the fight was drawn out, Kisame and Itachi were forced to retreat. It wasn't a total loss, though. Itachi had already made a mockery of Kurenai and incapacitated Kakashi before being forced back.
8 Itachi & Kisame Reappeared In Naruto's Hotel & Attempted To Abduct Him
While Kisame and Itachi may have been ousted by the jonin, they had hardly given up on their mission. After identifying Naruto's hotel, they prepared to abduct him in broad daylight.
In order to ensure that their plan went off without a hitch, Itachi cast a genjutsu on a local woman and got her to seduce and distract Jiraiya. In theory, this would buy the villains enough time to complete their mission before the Sannin came to check in on his student.
7 WINNER: Jiraiya Forced Itachi & Kisame To Leave Konoha Empty-Handed
Despite Itachi's clever trick, Sasuke bought Jiraiya enough time to make it back to the hotel and confront the two villains. Together, they posed a decent challenge but were swallowed in the belly of a toad.
While the Akatsuki members were strong enough to escape Jiraiya's prison, they knew that doing so would cause enough of a commotion to attract Konoha's reinforcements a second time. As a result, they were forced to flee from the village without anything to show for their efforts. Itachi's attempt on Naruto's life illustrated a pressing need for the Nine-Tails jinchuriki to become stronger.
6 Itachi & Pain Fought Against Killer Bee & Naruto
Itachi would have an opportunity for a rematch with Naruto after he was resurrected and enslaved by the Edo Tensei. Killer Bee backed up the future Hokage, while Nagato gave the fallen Uchiha as much assistance as the Rinnegan could afford.
The battle would be particularly important since Kabuto realized how valuable Naruto was to the Allied Shinobi Forces. Without Naruto winning his battles, the Five Nations wouldn't fare nearly as well against their zombified counterparts.
5 WINNER: Itachi Technically Won By Breaking Himself Out Of Kabuto's Spell
While Itachi did not manage to defeat Naruto or Killer Bee, his victory came in a different way. By casting a genjutsu on himself, he managed to escape from Kabuto's Edo Tensei and regain his own free will.
Now that Itachi's mind was once again his own, Nagato was significantly outnumbered and promptly defeated. Kabuto lost two of his most powerful thralls in the same skirmish, causing him extreme frustration and anger. While Itachi realized that his current condition was unnatural, there were things that needed to be done before he could find the peaceful rest he had worked diligently to earn.
4 Sasuke & Itachi Teamed Up Against Kabuto
While Sasuke had his own plans for the future of the world, he was still thankful for his brother's return and a chance to make amends for what happened between the two of them. However, there were more pressing concerns than a simple family reunion; Kabuto was still at large and needed to be dealt with if the heroes ever wanted to rid themselves of his Edo Tensei army.
Ultimately, the match pitted two skilled Sharingan users against a master of science and forbidden jutsu. Kabuto surprised the Uchiha brothers and audience alike with his competence.
3 WINNER: Itachi Defeated Kabuto By Casting The Izanami
Considering Kabuto's high durability, formidable healing factor, and impossible speed, it seemed as if there was no way to defeat him. Although the Susanoo kept the Uchihas safe, it was beginning to feel as if they were living on borrowed time.
Ultimately, Itachi won the fight by casting his own forbidden technique. By subjecting Kabuto to the Izanami, Itachi forced him to relive a loop of the fight until he realized the error of his ways and the cost of his hubris.
2 Sasuke Confronted Itachi For Murdering His Family & Clan
Ever since he was introduced, Sasuke's sole motive was to avenge his family and clan. He sacrificed everything in his quest for power, including his own village and even a nascent relationship with Sakura Haruno.
After Sasuke learned all he could from Orochimaru, it finally came time to enact his vengeance. He confronted his brother in a secret Akatsuki hideout while Suigetsu dueled with Kisame outside. The fight had only one potential conclusion; he would kill Itachi or die trying.
1 WINNER: Itachi Was Slain By Sasuke Uchiha
In the end, Sasuke had progressed enough to defeat his brother and find the vengeance he had worked so tirelessly to achieve. However, his victory could not have come without two pivotal factors.
Not only was Itachi suffering from a serious illness, but he also fully intended to let Sasuke kill him all along. Ever since he betrayed his clan, Itachi knew that his days were numbered and did everything in his power to cultivate Sasuke's potential as the next and greatest defender of Konoha.