Sasuke Uchiha is one of the strongest characters in Masashi Kishimoto's Naruto series. Along with Naruto Uzumaki, he stands on top as one of the greatest shinobi to ever live by the end of the story — and he didn't get there without sacrifice and effort.
Sasuke's journey to the top has been full of ups and downs, and he wasn't the strongest from the get-go. Over the years, he has faced countless adversaries. While he's conquered most of them, some have managed to break him and claim a victory of their own, against all odds. Here are a few fights where Sasuke didn't claim victory.
7 Versus Haku
One of Sasuke's first major battles came when he fought against Haku in Naruto's Land of Waves arc. Despite being a genius himself, Sasuke was met with quite a difficult challenge, one that he couldn't overcome even with Naruto Uzumaki's help.
Although he fared well against Haku, he wasn't strong enough to defeat him in a fight and, eventually, ended up falling to him. Thankfully, this triggered Naruto's Nine-Tails chakra, and he then proceeded to defeat Haku in battle himself.
6 Versus Gaara
The Chunin Exams arc of Naruto saw strong shinobi from all over the world gather in Konohagakure to take part in the titular Exams. Gaara was one of the absolute strongest there, if not the strongest, and was a target for Sasuke Uchiha. The two eventually clashed in the Finals of the exams.
While Sasuke did fairly well against him and even pierced the toughest of his defenses, he didn't have it in him to defeat Gaara, even when he turned to the power of the Cursed Seal. Once again, Naruto swooped in to save the day using his newly learned summoning jutsu.
5 Versus Itachi Uchiha
Sasuke's brother, Itachi Uchiha, was his target from the day of the Uchiha clan massacre until he finally learned the truth about him. The two faced off twice in the story, and while Sasuke did manage to triumph over Itachi the second time, their first fight was much less interesting.
Itachi easily dealt with Sasuke's Chidori, and Sasuke was beaten within a matter of seconds. What's more, Itachi used his Sharingan on him once again, and put him in a coma that only Tsunade Senju could save him from. Sasuke was simply no match for Itachi Uchiha at the time. This only pushed him to grow even stronger, and ultimately became one of the main reasons for him to leave Konohagakure.
4 Versus Killer Bee
Upon joining the Akatsuki, Sasuke was assigned the mission to go to Kumogakure and bring the Jinchuriki of the Eight-Tails, Killer Bee, to the organization. Sasuke paved his way to the heart of Kumogakure quite easily; however, defeating Killer Bee proved to be more than just a challenge.
Over the course of the fight, Sasuke got overwhelmed and was defeated by Bee not once but twice. Had it not been for his teammates, Sasuke would have died in Kumogakure. Eventually, Sasuke thought he managed to subdue the Eight-Tailsl however, Bee had actually tricked him and escaped to safety. As such, Sasuke's mission in Kumogakure effectively ended in a massive failure.
3 Versus The Five Kage
At the Five Kage Summit, Sasuke Uchiha attacked the representatives of all the five villages at once — and, as expected, he didn't fare well. Having already been beaten heavily by the Fourth Raikage, Sasuke was then put into a precarious situation by Mei Terumi. Following that, Onoki nearly killed him with his Dust Release jutsu.
Had it not been for Obito Uchiha, Sasuke would've died quite stupid and futile death in the Land of Iron. Thankfully, the right people were around him to save him when the time arrived. Truthfully, Sasuke lost more than just one fight at the Five Kage Summit. At the same time, though, he also managed to take down Danzo.
2 Versus Madara Uchiha
Sasuke Uchiha traded blows with Madara Uchiha quite a few times during the Fourth Great Ninja War. It goes without saying that he played a key role in saving the world. However, the first time Sasuke fought Madara, it didn't go according to plan.
With his Limbo shadows, Madara was easily able to subdue Sasuke. Using Sasuke's own sword, he proceeded to stab him through the chest, putting him in a near-death state. Thankfully, Sasuke was saved shortly after this defeat, and he then got an incredible power-up through the Sage of Six Paths.
1 Versus Naruto Uzumaki
Although Sasuke Uchiha emerged victorious when he first fought Naruto Uzumaki in the Valley of the End, their second fight was very different. Naruto, at this point, was stronger than he was. Even when Sasuke was actively trying to kill him, Naruto was actually trying to hold back.
Sasuke, despite using all that he had up his sleeve and even relying on the chakra of all nine Tailed Beasts, couldn't defeat his old friend. While the battle ended in a draw, Sasuke openly admitted his defeat and returned to Konohagakure to atone for his wrongdoings.