Naruto Uzumaki is the main character of Masashi Kishimoto Naruto series and an incredibly beloved character for fans. Naruto has defined the lives of a generation and continues to inspire countless people from around the world. His story is one that sees him go from a boy with limited talent to one who conquered the whole world and made everyone recognize him.
That said, Naruto wasn't always the capable 7th Hokage that he is today. In fact, on his way there he was faced with several difficult situations and he failed quite a few times. However, that failure is part of who he is today and has defined his entire being.
7
Failed to defeat Kimimaro
Naruto Uzumaki has fought several opponents over the years but few have managed to hold him off or stop him in battle. Kimimaro, one of Orochimaru's henchmen, managed to do just that. While Naruto was in pursuit of Sasuke, he was stopped by Kimimaro, and the two engaged in fierce combat where the young Uzumaki failed to break through his defenses.
Despite wanting to get to Sasuke immediately, Naruto failed. It wasn't until Rock Lee arrived that Naruto was able to chase Sasuke again and had that not happened he could have potentially lost the fight.
6
There was no stopping Sasuke
One of the obvious failures in Naruto's entire life is losing his fight with Sasuke and consequently allowing him to leave Konoha for good. This happened towards the end of the first part of the Naruto series. After Sasuke received the power of the Curse Mark from Orochimaru, he sought more power in an attempt to kill his brother, Itachi Uchiha.
Sasuke left with the Sound Five members and was then pursued by the members of the Konoha 11. Naruto eventually clashed with Sasuke in an attempt to bring him back to the village, but was unsuccessful.
5
Couldn't save Gaara
Shortly after the two and a half year time jump in Naruto, the Akatsuki began to make their move and their targets were none other than the Jinchuriki of the world. Gaara, being the Jinchuriki of the One Tail, was their very first target. Deidara and Sasori attacked the Hidden Sand Village and kidnapped him. Word was immediately sent to Konoha and Naruto's team immediately set out on a rescue mission. While they tried their best, they failed to save Gaara's life and he needed to be brought back to life later.

Naruto officially revives Jiraiya's Sage Mode in its new release
Jiraiya is one of the legendary Sannin in Naruto, and his iconic Sage Mode makes a comeback in the latest release.
4
Failed to beat Orochimaru
Naruto Uzumaki returned to his village after the time jump, having become incredibly powerful. Soon after, he started going on missions again and when he confronted Orochimaru on the Tenchi Bridge, he was given the opportunity to save Sasuke. Despite going into a frenzy and overwhelming Orochimaru, he was unable to defeat him to bring Sasuke back with him.
In fact, Sasuke was the one who ended up stopping him and showed him the true difference in strength that existed between the two. Naruto couldn't take down either Orochimaru or any of his minions.
3
Couldn't protect Neji
Neji was one of the members of the Konoha 11 and a genius of the Hyuga clan. He was an incredibly powerful ninja who wielded the power of the Byakugan. Neji was known to be a genius right from his birth. In fact, despite being a member of the branch, he had mastered several techniques in the main family.
As time went on, Neji continued to become a jonin, but he met his end during the Fourth Great Ninja War. The man who led him into the war could not save him from certain death. Neji's death was a reminder to Naruto that he can't protect everyone and that he would have to walk on the corpses of his own friends if he didn't have enough strength to protect them.
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2
Failed to save Obito
Obito Uchiha was one of the most important characters in the world Naruto. While he set out as a young boy with the goal of becoming Hokage, he ended up becoming a villain and the main instigator of the Fourth Great Ninja War.
Despite that, Naruto never lost faith in him and after his defeat he brought him over to the good side. From then on, Obito helped the Shinobi Alliance, but still ended up dying. The fact that he died in front of Naruto only shows that Naruto failed to keep him safe.
1
Failed to be the strongest
Naruto Uzumaki aimed to become the Hokage of the village and surpass every single one that came before him. It's fair to say that by the end of the story, he had already accomplished that in a beautiful way. Naruto was also the strongest shinobi in the world at this point, but that didn't last long.
During the Boruto era, Naruto can barely fight the likes of the Otsutsuki being. Also, he ends up losing the power of Kurama and is even weaker than several other shinobi around him. Undoubtedly, Naruto has failed to remain at the peak of his abilities long before reaching old age and that is truly a failure on his part.