Set in an Alternate Universe from the main continuity, the OVA tells the story of Naruto and his misadventures at the high school he attends as a transfer student. From the first day, he swiftly establishes a fierce rivalry with Sasuke, picks fights with every person he can, and fends off gangsters who would seek to defeat him. The story also outlines the three girls' reactions to Naruto's antics, as well as teasing the famous NaruHina ship somewhat.

All of Konoha mourns the tragic loss of Asuma Sarutobi. Knowing that Hidan and Kakuzu are bound to return, Shikamaru, Choji, and Ino prepare to head off to take revenge upon the duo while Kakashi takes temporary leadership of the team.

Taking place in the aftermath of the Kage Summit, Team Kakashi is sent out on a mission by Tsunade to a location known as "The Hole" to investigate an incident where its people were killed.

The Nine-Tailed Naruto clone tries to attack Dokku and the orphans, when Might Guy and Rock Lee arrive to repel it.

Naruto and Sasuke are enveloped in a huge, intense light after exchanging attacks. When they come to, scenes from their childhood unfold. Is this just a figment of their imagination? Or could this be the afterlife?

Naruto's wedding day approaches, and one by one, each of his friends is getting a gift ready. But the true purpose for this mission has not been revealed to anyone: the gifts will be judged to select who can attend the reception! Seeing the care and thought that went into each of the gifts, Kakashi begins to wonder if that's the right thing to do.