From its beginning in 2002 to its conclusion in 2017, the Hidden Leaf's knucklehead ninja has turned enemies into friends, friends into enemies, and achieved his lifelong dream of becoming the Hokage.
Through the duration of over 700 episodes, the Nine Tails Jinchuriki has tasted victory and wallowed in defeat, every battle carrying him closer to his destiny as the Hidden Leaf's leader. However, significant fights have defined Naruto both to the audience and to other characters in the story, and it's time to explore his greatest victories and most humiliating defeats.
10 Great Victory - Kiba
In his earlier days with Team Seven, Naruto fought Kiba in the first round of the Chunin Exams. Though the two share many similarities, Kiba ~ and the rest of the Genin at the time ~ viewed the fledgling ninja as a mere nuisance.
Therefore, it was a defining moment when Naruto defeated his canine counterpart. He utilized cleverness and ingenuity over the brawn and speed of his opponent, unlike many of the fights he engaged in Shippuden. It demonstrated Naruto as a formidable warrior and more competent than his oafishness might entail.
9 Humiliating Defeat - Orochimaru
During the ruse to capture Orochimaru and retrieve Sasuke, Naruto's poor restraint over his chakra would prove just as much his downfall as the mad scientist himself. It had been exactly what the Hidden Sound ninja had been hoping to bait him into, unleashing destruction widespread enough to put Sakura's life in danger.
Fortunately, Yamato was there to rescue her and contain the beast. However, not only would his targets escape, it indicated to Jiraiya that despite his intensive training between Naruto and Shippuden, he still had a way to go before he was ready to survive the Akatsuki, much more defeat them.
8 Great Victory - Pain
By the time Naruto had arrived to confront Pain, the village was already devastated. Kakashi was dead, the Leaf was in ruins, and Danzo was already preparing to usurp the Hokage. With what remained of his people watching, the upstart ninja confronted Pain and defeated him.
It was not without help. Hinata and the Toad Sages were both invaluable allies in his fight, though this is concurrent Asura's message of unity. When the dust cleared, Naruto had become more than a respectable ninja to the Leaf ~ he was their hero.
7 Humiliating Defeat - Sasuke's Retrieval
When Naruto and the other Genin set out to rescue Sasuke from the Sound Four, it's doubtful any would have considered their greatest obstacle would be Sasuke himself. Everyone played their role; Shikamaru strategically organized the squad, Kiba and Choji defeated their targets, and even Lee returned from the hospital to take on Kimimaro.
The only failure was Naruto's. Despite his strength as both the son of the fourth Hokage and the Nine Tails, he was unable to defeat Sasuke even though the latter had yet to fully refine his curse mark. It would take years before he would have another chance.
6 Great Victory - Kaguya
When the Otsutsuki rogue revealed herself and laid claim to the world's chakra, Team Seven was faced with their greatest challenge yet. Despite her tremendous force, instantly killing spears, and multidimensional magic, Naruto was able to defeat her and save the entire world.
What made this victory more significant was his collaboration with Sasuke to do so. Though the two had united against Madara, their combined efforts against Kaguya demonstrated that he might not only rescue the Five Nations, but the heart of his old friend along with them.
5 Humiliating Defeat - Madara
Under the will of the Madara Uchiha, the Gedo Statue consumed Kurama along with the other Jinchuriki, leaving Naruto gravely injured with no means of putting up a fight. He was rushed to Sakura for medical aid immediately, much to the horror of the Allied Shinobi Forces.
This loss was devastating in more ways than one. Not only was it suffered on the cusp of Madara's Infinite Tsukuyomi, but it also denied the Allied Forces their seemingly indomitable champion ~ the same champion which had saved all of their lives simultaneously with his chakra.
4 Great Victory - Gaara
The clash between the One Tails and Gamabunta would not only decide the fate of the Hidden Leaf, but its outcome would also produce invaluable allies to Konoha in their many battles to come. Through resourcefulness, creativity, and the assistance of the greatest toad sage, Naruto would secure a victory on a battle so destructive, there had been nothing like it in the series until that point.
Unusually, Konoha would not acknowledge him as much as they did in his success over the Six Paths of Pain, though it's likely because Naruto's mercy saved the entire village as opposed to merely Gaara.
3 Humiliating Defeat - Tobi
Naruto's first encounter with Tobi was equally as innocuous as it was embarrassing. The red cloud cloak he wore indicated him as an Akatsuki, but his zany, aloof mannerisms were enough to put him and his allies off their guard.
Despite the assistance of Sakura, Kakashi, Shino, Kiba, and even Yamato, none managed to land a scratch on their elusive opponent, who wasn't even trying to fight back. It illustrated that while Naruto might be strong, he was still far beneath one of the strongest antagonists in the series.
2 Great Victory - Sasuke Showdown
The final fight between Naruto Uzumaki and Sasuke Uchiha shaped valleys and created craters, allowing the audience a glimpse of how far both boys had become since the series began.
While the battle may have ended in a stand-still, a tie was all Naruto needed to finally bring his friend back to the light. Sasuke's philosophy was to rule the world through his exclusive power alone, and once it was proven that he would never be the strongest no matter his depravity, he finally rejoined his friends in Konoha.
1 Humiliating Defeat - Kabuto
Until Naruto's fight with Kabuto, his heroism bore positive results. He courageously saved Kakashi from Zabuza's water prison, rescued Sasuke from Gaara's clutches, and was even willing to protect Iruka to his dying breath.
The Sannin battle between Tsunade, Jiraya, Orochimaru, Kabuto, and Naruto would not share these favorable results. While Naruto managed to prevent the medical ninja from striking a killing blow to Lady Tsunade, it would cost him dearly in the process, forcing him from the rescuer to the rescued.