Shippū! Konoha Gakuen Den!

is the fifth Naruto OVA.

Behind the Scenes
It is an OVA Gaiden (alternate history) made by Studio Pierrot and was released with the Naruto: Shippūden DVD 7 in Japan. This fan-service OVA is not animated: it is narrated through a series of still cells, based on the still cells that were used for the second Naruto: Shippūden ending.

Synopsis
The history is completely narrated by Sakura Haruno, Ino Yamanaka and Hinata Hyūga, but sometimes Naruto Uzumaki and Sasuke Uchiha say their own dialogue. The story is about the brawler Naruto (who uses yo-yo techniques) after he is transferred to Konoha High School. Naruto's dream is be the souban (leader of Yakuza) of all Japan. The Naruto-Sasuke kiss that happens in the series is not present in the OVA. Instead, Naruto's pants get stuck when jumping while fighting Sasuke, and in the next cell, Sasuke is cleaning his mouth and Naruto is putting his pants on, both of them incredulous and furious about what just happened.

Most of the story is about how Naruto defeats, one after another, the most prominent fighters in the school, including:
 * Local gang leader (who doesn't have a counterpart in the manga).
 * Kiba Inuzuka.
 * Rock Lee, who is the school's cool soccer star.
 * Sumo Fighter Chōji Akimichi (after calling him a fatty).
 * Karate Shotokan expert (and a tomboy) Tenten.
 * Class President Neji Hyūga, the best martial artist in school.

This turns Konoha High into a chaos, and teachers Kakashi Hatake, Kurenai Yūhi, Asuma Sarutobi, or headmistress Tsunade can't do anything about it. When Naruto has defeated everyone at school with the exception of Sasuke Uchiha, the local gang leader lures him by kidnapping Hinata, Ino, and Sakura. Naruto tries to free them but the gang threatens to harm the girls if he fights back. Naruto is beaten badly until he enters Tailed Beast state. However, we never actually see him fighting with this power-up because at that moment, Sasuke, Shikamaru, Kiba, Chōji, Neji, Lee, and Shino come to help him. This event marks the start of their friendship.

The next day, Hinata, who has a crush on Naruto, invites him on a date. This date is interrupted by all their friends who were spying on them as Hinata falls over Naruto. Embarrassed, Hinata runs without telling Naruto her feelings. At this point, it is hinted that everything had a happy ending.

However, as a sort of epilogue, or sort-of events that would happen in the next episode, we are told quickly of more events-to-happen:
 * The school enters another state of chaos because principal Tsunade had been using the school's money for gambling.
 * Iruka Umino a new teacher who appears to have a relationship with Naruto, is hired.
 * A new gang, Akatsuki, appears to attack Naruto.
 * Konoha High School will face against the Suna High School's nerds: Gaara, Kankurō, and Temari.
 * There appears to be some relationships between Sasuke and an Akatsuki member named Itachi.
 * Transvestites Orochimaruko (Orochimaru in original manga) and Kabuko (Kabuto in original manga) come looking for Sasuke… and Sasuke goes with them!!! (with unknown purposes).
 * New transfer student Sai appears and follows Naruto everywhere, wanting him to be the subject of his drawings, much to Naruto's disgust.
 * The final showdown between Naruto and Sasuke will soon start!

At the very last moments of the OVA, it is revealed why Sakura cut her long hair at the end of the second Naruto: Shippūden ending; because a bit of chewing gum got into it.

Trivia

 * An omake of Naruto: Shippūden episode 59, animated versions of "Konoha High" Naruto, Sasuke, and Sakura were shown on a sidebar.
 * Naruto and Sasuke from this special are separate unlockable characters in the PSP game Naruto Shippūden: Ultimate Ninja Heroes 3.
 * The dress that Hinata wears during her date with Naruto looks similar to the dress Kishimoto used for the first concept art of her.