Shippū! Konoha Gakuen Den!

is the fifth Naruto OVA.

Behind the Scenes
The OVA was made by Studio Pierrot and released with the Naruto: Shippūden DVD 7 in Japan. The OVA is not animated; it is told through a series of still cells, based on the still cells that were used for the second Naruto: Shippūden ending. The story is completely narrated by Sakura Haruno, Ino Yamanaka and Hinata Hyūga, although Naruto Uzumaki and Sasuke Uchiha sometimes say their own dialogue.

Synopsis
The new transfer student at the prestigious Konoha High School, Naruto Uzumaki, arrives and announces his ambition to become the Sōban (Yakuza leader) of all Japan, developing a rivalry with Sasuke Uchiha in the process. A local gang leader and his followers later come to settle their differences with Naruto, but are defeated by the latter's yo-yo-based techniques. Naruto then challenges the toughest people in the school to fight him, sending the school into chaos, with faculty members Kakashi Hatake, Kurenai Yūhi, Asuma Sarutobi, Ebisu, and the principal, Tsunade, watching from afar.

Naruto then defeats, one after another, the most prominent fighters in the school, including:
 * Kiba Inuzuka, who detests Naruto.
 * Rock Lee, the school's hot-blooded soccer star.
 * Chōji Akimichi, who Naruto referred to as "fat".
 * Tenten, a tomboyish Karate practitioner.
 * Class President Neji Hyūga, the school's number one martial arts expert.

The narrators speculate that Naruto's reason for staying in the school after these victories is to challenge Sasuke, since the two had gotten into a fight on the day of Naruto's arrival and held several competitions since. As an act of revenge, the defeated gang leader has his men kidnap Sakura, Ino and Hinata, unable to defeat Naruto in a fair fight. Naruto attempts to save the three but is defeated by the gang's dirty tactics. Sasuke, along with Neji, Kiba, Lee, Chōji, Shikamaru Nara and Shino Aburame, arrive in time to defeat the gang members, with Naruto and Sasuke subsequently shaking hands. Naruto and Hinata later go on a date, with their classmates spying on them throughout.

The narrators state that everything had a happy ending, but then mention a series of other troubling events yet to come:
 * The school's management is in crisis, with rumours stating that principal Tsunade had been using the school's money for gambling loans.
 * Iruka Umino, who appears to be involved in Naruto's personal life, is hired by the school.
 * Various assassins attack, one after another.
 * A threat presses in from the neighbouring town's Suna High School: Gaara and his cronies, Kankurō and Temari, wearing nerd-like attires.
 * The mysterious group called Akatsuki has their sights set on Naruto and throw the school into chaos.
 * There appears to be some relationship between Sasuke and the Akatsuki member named Itachi.
 * The Akatsuki leader's grand ambition will be revealed.
 * Transvestites Orochimaruko and Kabuko come looking for Sasuke. Sasuke later disappears, possibly going with the two.
 * New transfer student Sai appears and follows Naruto everywhere, wanting him to be the subject of his drawings, much to Naruto's disgust.
 * Naruto and Sasuke will have their final showdown.

At the end 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 stuck in it.

Trivia

 * In the omake at the end of Naruto: Shippūden episode 59, animated versions of "Konoha High" Naruto, Sasuke, and Sakura are shown on a sidebar.
 * Naruto and Sasuke from this special are separate unlockable characters in the PSP game Naruto Shippūden: Ultimate Ninja Heroes 3.
 * Naruto, Sasuke, Sakura, Kakashi, Ino, and Hinata from this special all appear as DLC costumes in Naruto Shippuden: Ultimate Ninja Storm 3.
 * The dress that Hinata wears during her date with Naruto looks similar to the dress Masashi Kishimoto used for the first concept art of her.