Naruto: The an initial 10 characters Sasuke lost To (& How) Sasuke Uchiha is among the most an effective shinobi in the Naruto series, however that wasn"t constantly the case. Here are the an initial characters Sasuke shed to.

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Haku, Sasuke and Orochimaru
Sasuke Uchiha is just one of the most powerful shinobi in the Naruto series, but that wasn"t constantly the case. The critical survivor that the Uchiha clan may have been the most expert genin in ~ the beginning, however he has taken some losses in the original series that part fans may have actually forgotten as the manga continued.

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From Team 7"s very first battle versus Zabuza and also Haku to Sasuke"s war while he was on the route of an avenger and also villain in Naruto Shippuden, below are the very first characters he shed to in the collection and how, from very first to last.

The broken Seal is the 16th illustration of Naruto, and also the resource of the well known image of Sasuke protecting Naruto because that the an initial time in the series. Although Naruto and Sasuke have actually done nothing yet fight up until this point, they are in the midst of battling Haku that has them trapped in his Kekkei Genkai, Demonic Mirroring ice Crystals.

After Haku notices that Naruto is open up for an attack and also throws senbonーmetal needles the are mainly used by clinical ninjasーat him, Sasuke move to defend Naruto from the assault, resulting in his very first loss in the series.

Orochimaru's first appearance on the right, Sasuke utilizing Sharingan ~ above the left
Orochimaru"s an initial appearance before Sasuke was episode 30 of Naruto and also during the Chuunin Exams arc whereby he went undercover as a woman ninja named Shiro, a genin from the town Hidden in the Grass. Throughout the long and grueling battle, Sasuke"s Sharingan activates and he uses Fire Release: Dragon Fire technique to end the battle.

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However, Shiroe reveals it s her to be Orochimaru, and he bites Sasuke"s neck, leaving him v the Cursed Seal that Heaven.

Late because that The Show, yet Ready come Go! The can be fried Secret technique Is Born was episode 67 of Naruto. Their fight was from illustration 67 to 68. Sasuke and Gaara"s fight has actually been the controversy of numerous topicsーdid Sasuke success or to be it Gaara? when their battle was interrupted, it ongoing on even as the town was under attack.

While Sasuke came to be the 2nd person come pierce v Gaara"s Absolute Defence v Chidori, Sasuke ultimately ran the end of chakra in the end, through Gaara still having some since of Shukaku. While that was more of a tie, some argue Sasuke lost.

7 Itachi Uchiha (Hate among The Uchihas: The last Of The Clan!)

Hate amongst The Uchihas: The last Of The Clan was episode 85 0f Naruto and the resource of the "Choking Sasuke" meme that exploded in popular in 2019.

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This was more of a beatdown instead of a fight, considering how easily Itachi deflected Sasuke"s attack and proceeded to press him versus the wall. Itachi climate puts Sasuke in a Tsukuyomi and forces him to relive their parents and clans" deaths to make him stronger, albeit in a twisted way.

A Fierce fight Of roll Thunder was episode 105 of Naruto and a filler episode many fans most most likely cannot remember. Nonetheless, this is a struggle Sasuke lost. Aoi Rokushou to be a ninja indigenous Amegakure the both Naruto and also Sasuke fought. Once Sasuke offered Chidori ~ above Aoi"s sword, however, he to be repelled backward.

When he provides his jutsu once again and Aoi taunts Sasuke around his clan"s massacre, the is deflected and also thrown turn off the bridge. In the end, Naruto was the one who eliminated Aoi by leading to him to autumn off a cliff from the influence of his Rasengan.

5 Killer B (The Eight-Tails VS. Sasuke)

The Eight-Tails VS. Sasuke was episode 143 of Naruto Shippuden. While Killer B may have been supplied as a hoax character up till this fight versus Sasuke, Suigetsu, Juugo, and also Karin, this fight confirmed their differences in strength.

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Killer B would have killed Sasuke with his Lightning Release: Lariat if the wasn"t because that him utilizing Karin"s cure Bite and Juugo using his Cellular regeneration Ejection on him. Sasuke practically died together it ruptured his organs, neck, and also chest, leave him come lie there dying until his left eye becomes the Mangekyo Sharingan and also he makes use of Amaterasu and Chidori spicy Spear come knock Killer B unconscious.

Power that The five Kage was illustration 204 of Naruto Shippuden. No matter how strong of an adversary Sasuke was, attempting come fight every 5 Kage at as soon as was a stupid and arrogant decision. The fight involved a close as soon as they began using their progressed jutsu. After ~ the 5th Mizukage supplies two Kekkei GenkaiーLava Release and also Boil Releaseーand almost kills him, she is limit by White Zetsu.

Near the end when that runs out of chakra, thee Tsuchikage uses Dust Release: losing of the Primitive World method to try and end him, yet Tobi conserves him at the last 2nd and uses Kamui come teleport them the end the room.

3 Madara (A True Ending)

A True Ending is episode 393 of Naruto Shippuden. This is not lot of a fight, as this scene was consisted of to display how an effective Madara was as an antagonist. After ~ Sasuke rejoins the battle, he arrives at where Madara is to start battling him.

However, before he have the right to do anything, Madara raises Sasuke in the air and stabs him with the chest.

The last Battle is episode 476 of Naruto Shippuden. This is the fateful fight every fans were awaiting, the second half the Naruto and Sasuke"s fight from the first season of Naruto where Sasuke won in the valley of the finish when they to be children. Their fight is from illustration 476 come 478, The Unison Sign.

After fighting because that what appears like whole day non-stop, both Sasuke and also Naruto shed their arms. At the end of the fight, Sasuke admits the he shed the battle. Despite Naruto stating that it isn"t about winning or losing, it was a declaration from Sasuke himself.

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1 Momoshiki Otsutsuki (Boruto: Naruto The Movie)

The fight against Momoshiki Otsutsuki differs from the Boruto anime to Boruto: Naruto the Movie. 

While Sasuke won his fight versus Kinshiki Otsutsuki by using his Rinnegan skillfully, he can not go against both Kinshiki and Momoshiki there is no running out of chakra, resulting in Sasuke using Rinnegan come teleport to safety.

NEXT: Naruto: 5 times Sasuke to be Wrong (& 5 time He was Smarter than We assumed He Was)

Brianna Albert is one author, writer, reader, and seasonal anime watcher. She has actually been watching anime because before Naruto became Hokage and trying to figure out just how to bend air due to the fact that she remained in kindergarten. She now works because that Valnet, Inc, writing anime lists on Comic publication Resources, writing around television ~ above Screenrant, and editing as a small Editor. In she spare time, she writes romantic novels, works as a freelance Japanese translator, records hearts in otome games, and also binge watches K-Dramas. You can follow her and also her witty tweets at