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Shippu! Konoha Gakuen Den is a less-than-eight-minutes-long Gaiden (alternate history) made by Studio Pierrot. The Gaiden was released with the Naruto Shippuden DVD 7 in Japan. It is not animated: it is narrated through a series of still cells based on the still cells that were used for the second Shippuden ending.

Plot overview:
The history is completely narrated by Sakura Haruno, Ino Yamanaka and Hinata Hyuga, 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 Yakuzas) of all Japan. The Naruto-Sasuke kiss that happens in the series is not present in the Gaiden. 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 soccer star.
* Sumo Fighter Choji Akimichi (after calling him a fatty).
* Karate Shotokan expert (and tomboy) Tenten.
* Class President Neji Hyuga, the best martial artist in school.
This turns Konoha High into a chaos, and teachers Kakashi Hatake, Kurenai Yuhi, 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 Nara, Kiba, Choji, Neji, Lee, and Shino Aburame 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 Sand High School's nerds: Gaara, Kankuro, and Temari.
* There appear 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 Gaiden, it is revealed why Sakura cut her long hair at the end of the second ending of Naruto Shippuden: because a bit of chewing gum got into it.