The Legendary Sannin were the students taught by Hiruzen Sarutobi of the Naruto universe. Each of them had incredible strength and were considered to be roughly as strong as Kage. Moreover, they played a role in teaching the members of Team Seven, all of whom would become stronger than they were.
Through the series, the three ninja have had an abundant number of opportunities to prove their worth against their foes. Through identifying the Sannin's best fights, we gain a better understanding of why the organization is respected and feared across all five of the great nations.
10 Orochimaru's Fight Against Sasuke Was Brief But Meaningful
After years spent training under Orochimaru, Sasuke was finally ready to pursue his brother for the vengeance he desperately craved. There was only one problem: he was still expected to fulfill his obligation as the Sannin's next vessel.
Taking advantage of his master's weakened state, Sasuke attacked Orochimaru in his bed and struck him with a chidori. The villain wouldn't go down without a fight; with the last of his strength, he transformed into a massive white snake and nearly defeated his former apprentice.
9 Jiraiya Fought Naruto To Get Him Under Control
Controlling Kurama may have had enormous benefits, but it wasn't easy. In order to better prepare for the Akatsuki's looming threat, Jiraiya instructed his student to harness the Nine-Tails' chakra. Predictably, he lost control and lashed out against his mentor.
Considering Jiraiya's tremendous skill (and the fact that Kurama was not completely formed), he was able to revert Naruto back to his original state. However, the Sannin still regarded the encounter as a harrowing one, even if it showed that Naruto's potential was almost limitless if honed.
8 Orochimaru's Fight Against Log Proved That He Had More Than Ninjutsu Up His Sleeve
After Orochimaru's alleged redemption to the Leaf, he came across and fought a ninja known as "Log." A frightened Mitsuki watched the exchange of swords nervously, with both combatants evenly matched.
This fight was particularly unique since Orochimaru relied mostly on taijutsu in order to defeat his opponent. In the end, he won by slipping a small, poisonous snake through the gaps of Log's armor and paralyzing him. While the rogue ninja may have made amends with his village, his means of victory indicate that he still hasn't forgotten his underhanded tactics.
7 Orochimaru Fought Team Seven In The Forest Of Death
After hearing Kabuto's report about Sasuke, Orochimaru was intrigued and confronted him in the Forest of Death. Having assumed that Orochimaru was simply another contender, the young genin failed to realize that they were significantly outclassed.
In addition to defeating Sasuke and knocking him unconscious, Orochimaru delivered a curse mark that Sasuke would carry with him for the remainder of his life. It bestowed him with a significant boost of strength and was intended to entice him into the fallen Sannin's service.
6 Tsunade & Jiraiya Teamed Up Against Orochimaru & Kabuto
After being severely crippled by Hiruzen Sarutobi, Orochimaru went to Tsunade and asked that she heal his arms. After great consideration, Tsunade declined her former friend's request. Predictably, Orochimaru did not take this well.
Jiraiya soon joined the fray, and a massive fight broke out between the three Sannin. Although Orochimaru fared well against the heroes with Kabuto's assistance, he was ultimately defeated and forced to retreat. Shortly after, Tsunade agreed to become Hokage, having demonstrated a willingness to put her village above all else.
5 Tsunade Faced Madara Alongside The Other Four Kage
Having realized how valuable Naruto was to the Allied Shinobi Forces, the Five Kage agreed to confront (and hopefully, defeat) Madara by themselves. Considering how fundamentally different they were, the world leaders performed remarkably well against their mutual enemy. Tsunade even managed to fracture the villain's Susanoo.
However, Madara was able to summon many more and quickly overwhelmed his adversaries. Tsunade couldn't outlast him even with the benefit of her hundred healings chakra seal. In the end, their synergy wasn't much of a challenge for the raw power that Madara wielded, and his reckoning with Naruto was inevitable.
4 Orochimaru Was Forced To Retreat After Naruto Harnessed Kurama's Power
When the heroes heard about Kabuto's rendezvous with "Sasori," they didn't want the opportunity to go to waste. Naruto quickly confronted the villain in hopes of forcing him to share Sasuke's location.
This resulted in a battle with Orochimaru, one where the Jinchuriki's natural rage and desire for victory compelled him to draw upon Kurama's power. While it was enough to deter the fallen Sannin, he became a danger to his friends and might have accidentally killed Sakura if Yamato didn't seal him.
3 Jiraiya Overcome Both Kisame & Itachi
When the Akatsuki came to Konoha in order to abduct Naruto, Jiraiya was hot on their trail. He came to his pupil's aid at the hotel the villains encroached upon and trapped them within a toad's stomach. Having failed to anticipate the Sannin's presence, they were forced to flee in an act of self preservation.
Their decision to retreat may not have been exclusively because they felt they couldn't take Jiraiya down in a fight. Due to the commotion that they had caused on the Leaf's borders, they didn't want to attract any further attention to themselves and risk being caught.
2 Orochimaru Assassinated Hiruzen Sarutobi At The End Of The Chunin Exam
When the Sand officially began its invasion of the Leaf, Orochimaru knew it was time to make his move. Having posed as the Kazekage, he used his proximity to Hiruzen Sarutobi in order to attempt taking his life.
The Sound Four prevented any shinobi from assisting their leader by erecting an indestructible barrier around the rooftop. While Hiruzen would ultimately be defeated by his former student, he managed to seal away his arms, thereby forbidding him from weaving hand signs. Consequently, Orochimaru was too weakened to finish Konoha off and retreated instead.
1 Jiraiya Faced Pain & Died In The Rain Village
When Jiraiya had a suspicion of Pain's identity, he knew what needed to be done. The Sannin entered the Rain Village alone and faced off against both the Akatsuki leader and Konan.
Despite being vastly outnumbered, he performed moderately well. Jiraiya defeated several of Pain's bodies before being taken by surprise and (literally) disarmed. With his dying breath, he conveyed the secret behind Nagato's power to the Leaf and the only way he might be permanently defeated. Naruto would later use this knowledge to save all of Konoha and surpass his mentor's wildest dreams for him.