As the main character of his series, Naruto has fought and defeated a lot of powerful characters, most of whom were skilled shinobi. That said, he has lost to several characters, too. Some of Naruto's losses were comical, but others were far more serious, and he would have died if other people had not saved him.
Most of the Naruto Characters who defeated Naruto were Kage-level fighters. In fact, one character was an alien being, while another was a vessel for an even stronger being. Many of these losses occurred before the timeskip when Naruto was still a Genin, but he also lost some fights as an adult, even after becoming Hokage and being recognized as one of the strongest ninja in history.

7 Naruto Characters Who Would Lose to Boruto Uzumaki
Even Naruto's strongest characters cannot compete with Boruto's level. They would lose to him in a heartbeat.
9
Rock Lee
Rock Lee has become one of Naruto's closest friends, but when they first met, Naruto was not a fan. This meeting occurred before the Chunin Exams began, and it resulted in Naruto challenging Lee to a fight. Naruto did not like that Lee challenged Sasuke to a duel so brazenly, and he was jealous because Lee confessed that he liked Sakura. Unfortunately, Naruto did not last long. In fact, he was beaten very easily.
Lee may not be able to use ninjutsu or genjutsu, but he has mastered taijutsu, including the Eight Gates, which is one of Naruto's most unique powers. He did not need to use any of the Inner Gates against Naruto though. Lee simply brushed Naruto's punch aside with his fingers and hit him with a Leaf Whirlwind leg sweep which sent him comically spinning into a wall. Fortunately, Naruto's taijutsu improved as the series went on.
8
Tsunade
Tsunade is one of the Leaf Village's Three Legendary Sannin. When Naruto first met her, she was still considered the world's strongest medical ninja. She possesses a powerful life force and great superhuman strength, and she has mastered Mitotic Regeneration, which essentially makes her immortal during fights. Tsunade became the 5th Hokage after meeting Naruto, but before becoming one of the Naruto franchise's legendary Kage, she had a cynical and disrespectful view of her predecessors and their sacrifices.
Naruto did not like her attitude and challenged her to a fight. Tsunade agreed and vowed to fight Naruto using a single finger. She easily dodged Naruto's attacks and sent him flying after flicking his forehead. Naruto tried to beat her with the Rasengan, but Tsunade ended the fight by slamming her finger into the ground. This caused the Rasengan to recoil and Naruto got stuck in the ground fissure that her finger created.

Naruto: 10 Characters That Have Regenerative Abilities
Regenerative abilities give these Naruto characters an edge in all fights.
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Kakashi Hatake
Kakashi was considered a generational prodigy, which explains why he became a Jonin when he was just 12 years old. There are very few anime sensei that rival Kakashi because he personally trained Naruto, Sasuke, and Sakura, who all went on to become Kage-level shinobi. He also became the 6th Hokage shortly after the Fourth Great Ninja War, and despite no longer having his Sharingan, his strength continued to increase to the point he could fight other Kage.
Kakashi handed Naruto his first, and arguably most embarrassing, defeat during the bell test. Naruto wildly charged at Kakashi, who was reading Make-Out Paradise at the time. Kakashi easily blocked Naruto's punch and dodged a kick before appearing behind Naruto and striking him with the Thousand Years of Death technique. Naruto then tried to overwhelm Kakashi with Shadow Clones, but Kakashi forced Naruto to attack himself instead. The fight officially ended with Naruto getting trapped in a snare in comical fashion.
6
Orochimaru
As one of the Legendary Sanin, Orochimaru is one of the strongest ninja in history. He was one of the few characters from the Leaf Village who were strong enough to become Hokage. When Naruto first encountered him, Orochimaru was pretending to be a Genin from the Hidden Grass Village, and they briefly clashed in the Forest of Death during the second phase of the Chunin Exams. At the time, Naruto had just started accessing some of the Nine-Tailed Fox's chakra.
Naruto used the Tailed Beast's power to pummel one of Orochimaru's giant snakes, and then stopped it from attacking Sasuke with a pair of Kunai. While holding the snake back, Orochimaru wrapped his tongue around Naruto and brought him close. Orochimaru then used the Five Pronged Seal to seal the Nine-Tail's power, which knocked Naruto out instantly. Naruto got tossed immediately afterwards, and if Sakura had not saved him, he would have died from the fall.
5
Sasuke Uchiha
Naruto and Sasuke are like brothers, but they also had one of the greatest anime rivalries of all time. They fought several times over the course of the series, and these fights typically ended in a draw, but their first battle in Final Valley saw Sasuke come out on top. This was easily the best pre-timeskip fight, and it ended with a clash between Sasuke's Curse Mark Level 2 empowered Chidori and Naruto's Nine-Tails enhanced Rasengan.
Naruto chose to hit Sasuke's headband instead because he did not want to kill him, while Sasuke negated the Chidori in time to spare Naruto's life. He still knocked Naruto out though. Sasuke went on to become a god-tier ninja who can defeat threats as powerful as Kaguya Otsutsuki, alone. With the Eternal Mangekyo Sharingan, Susanoo, and Rinnegan, Sasuke can take down all the Tailed Beasts and the previous Five Kage at once if he wanted to.

The 7 Most Badass Naruto Fights of All Time, Ranked
Let's take a look at the 7 most badass Naruto fights of all time ahead of the 2026 anniversary specials.
4
Pain
Nagato, otherwise known as Pain, was the leader of the Akatsuki, and he personally destroyed the Hidden Leaf Village while searching for Naruto and the Nine-Tails. Pain mastered the Rinnegan and all six of its Paths, making him the most powerful shinobi outside of the Five Great Nations. As a result, Pain could summon powerful beasts, absorb ninjustu, manifest advanced weapons, manipulate souls, govern life and death, and control gravitational forces. Nagato split these powers between six bodies, which all shared a field of vision.
Naruto defeated five of Pain's bodies using Sage Mode, the Rasenshuriken, and Rasengan, while the Asura Path was smashed into pieces with a single punch. The Deva Path proved to be the most troublesome, as it used Almighty Push and Universal Pull to ultimately pin Naruto to the ground, defeated. If Pain had not injured Hinata in front of Naruto, Naruto would have likely not released the Nine-Tail's power and broken free. It's true that Naruto went on to beat Pain, but their first fight ended in Naruto's loss.
3
Madara Uchiha
Madara is arguably the strongest Uchiha in history, and he probably could have defeated both Naruto and Sasuke during the Fourth Great Ninja War with his Six Paths Ten-Tails Jinchuriki form, which is one of the most powerful transformations in Naruto. He was stronger than the Five Kage and wiped out thousands of shinobi during the war with a single jutsu. Only Hashirama Senju, a legendary ninja god, was powerful enough to beat him.
Madara never fought Naruto in a one-on-one fight, which was probably for the best because Naruto would have likely not stood a chance against a Sunsanoo user like Madara who also mastered the Rinnegan and Wood Release. Madara faced Naruto and the nine Tailed Beasts alone, and he successfully sealed the Tailed Beasts in the Gedo Statue. Naruto was knocked out instantly when the Nine-Tails was removed from his body, and he would have died if Sakura had not kept him alive with her medical ninjutsu.
2
Momoshiki Otsutsuki
Momoshiki is part of the Otsutsuki Clan's main family, and his plan was to use the Nine-Tail's chakra to create a new Chakra Fruit since Kaguya had failed. Unlike Kaguya, Momoshiki was a highly skilled taijutsu user who could fight adult Naruto and Sasuke at once for a short time before being overwhelmed.
Momoshiki possessed the Byakugan, which allowed him to strike a person's chakra points while benefitting from a near 360° field of vision. The Rinnegan in his hands gave him the ability to absorb, enhance, and unleash powerful ninjustu attacks. If left unchallenged, these attacks could wipe out an entire village. Naruto was strong enough to beat base Momoshiki one-on-one, but he allowed himself to be beaten and captured in order to protect his son and reduce collateral damage to the Leaf Village. It may have been intentional, but a loss is still a loss.

Naruto: 7 Characters Who Can Resist Itachi's Tsukuyomi
Itachi's Tsukuyomi is a deadly genjutsu, yet these Naruto characters could potentially resist it.
1
Jigen
As its leader, Jigen was the strongest member of Kara, but he was a lot more than an ordinary monk. He was actually the temporary vessel of Isshiki Otsutsuki, Kaguya's former partner. Naruto was the 7th Hokage when Jigen appeared in the village looking for Kawaki, and it became clear from the beginning that Naruto was weaker.
Naruto fought Jigen in another dimension with Sasuke, and they were easily overwhelmed. Jigen took out dozens of Naruto's Shadow Clones, which were all using Nine-Tails Chakra Mode. When Jigen got serious, he destroyed Sasuke's complete Susanoo with a single kick. Not only did Jigen dodge all of Naruto's Tailed Beast Mode attacks, he destroyed the transformation as easily as Sasuke's Susanoo. Jigen ended the fight by impaling Naruto with black rods and sealing him, while Sasuke escaped to warn the village.
- Release date
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October 2, 2002
- Network
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Adult Swim