Sasuke Uchiha is one of the main characters in Masashi Kishimoto's Naruto series. Introduced in the very beginning as a survivor of the Uchiha Clan massacre, Sasuke soon became a member of Team 7, alongside Naruto Uzumaki and Sakura Haruno.
As such, Sasuke was a part of the main cast of the Naruto series. Over the years, he has gone on to achieve greatness just like Naruto did, however, just like his counterpart, Sasuke has also been met with failure on more than one occasion. While Sasuke did end up dealing with them one way or another, he failed quite often on his journey to where he is today.
7 Failed To Beat Gaara
Sasuke Uchiha was deemed to be a genius at the very beginning of the story and, to grow stronger, he always wanted to combat the strongest of enemies. During the Chunin Exams, Sasuke was faced by Gaara of the Hidden Sand Village and while he did put up quite a good fight against him, even pushing his body beyond its limits, he failed to defeat him.
It was Naruto who ended up saving the day and defeated Gaara in quite an incredible fashion. Sasuke fell one step behind his best friend towards the end of that arc.
6 Failed To Beat Orochimaru
The Chunin Exams was a battlefield for the strongest of shinobi to gather and work towards becoming stronger and gaining higher ranks as ninja. Sasuke, along with every other member of Team 7, took part in the Chunin Exams as well.
However, they were faced with an incredibly powerful adversary, Orochimaru. In the Forest of Death, Sasuke and Naruto fought against Orochimaru and both of them ended up failing. Undoubtedly, Sasuke put up a better fight against the member of the Legendary Sannin than Naruto, however, he still failed to take him down, at the end of the day.
5 Failed To Kill Itachi
For the majority of his teenage years, Sasuke only had one goal in mind and that was to kill his older brother, Itachi Uchiha. Itachi was the man responsible for murdering the Uchiha plan and, more importantly, his very own family. As such, Sasuke wanted to exact revenge on him by becoming strong enough to actually be able to kill him.
While Sasuke did get to become tremendously powerful, surpassing even some members of the Akatsuki, he wasn't strong enough to kill his brother when the two clashed. Itachi let Sasuke win and, in the process, freed him from Orochimaru's curse.
4 Failed To Understand The Meaning Of Shinobi
Every Shinobi learns as they progress on the path of life. Sasuke's case was no different. While growing up, Sasuke was dyed multiple colors by different people who wanted to use him, and, as such, he often strayed from the right path. In fact, Sasuke even wanted to destroy Konoha at one point and failed to understand what it truly meant to be a shinobi.
It wasn't until the 4th Great Ninja War that Sasuke finally understood the meaning behind this word. After meeting with the four Hokage, Sasuke learned about the history of shinobi and finally understood what it truly meant to be one and persevere.
3 Failed To Kill Madara
Madara Uchiha was the ultimate antagonist in the Fourth Great Ninja War before he was taken out by Black Zetsu in an attempt to bring back Kaguya Otsutsuki. Being the ultimate threat, Madara was fighting the entirety of the Shinobi Alliance by himself. Expectedly, he came across Sasuke at one point, and while he did have admiration for the young Uchiha, to him, he was not a threat.
Madara dealt with Sasuke easily and the young Uchiha's attempt to vanquish the ghost of the Uchiha failed terribly. He was stabbed right through his chest and left to die. Eventually, he was saved by Kabuto Yakushi.
2 Failed To Become Hokage
After his conversation with the four Hokage, Sasuke finally understood what it truly meant to be a Shinobi and, at the same time, came up with a new goal. Sasuke now wanted to be the Hokage of the village. Upon arriving on the battlefield to aid the Shinobi Alliance, Sasuke announced his goal to become Hokage.
This meant that he would be in direct competition with Naruto Uzumaki. Later on, the two clashed in the Valley of the End, and, there, Naruto defeated Sasuke. With that, Sasuke finally returned to his senses and decided to follow Naruto and help him fulfill his dream. As such, he never worked towards becoming the Hokage ever again. Despite that, Sasuke is known as the Other Hokage today.
1 Failed To Kill Naruto
Upon deciding that he would become the new Hokage of Konoha, Sasuke knew that he had to get rid of the last obstacle standing in his way, his best friend, Naruto. To accomplish that, he fought against his best friend in the Valley of the End and threw everything he had up his sleeve at the young Uzumaki.
Expectedly, the two were evenly matched in this fight, however, in the end, Naruto was the one who emerged victorious. Sasuke failed to kill his best friend and instead chose to follow him for the rest of his life, trying to maintain the peace that he would later go on to create.