While the first four episodes deal with the childhood of some main characters, the rest of the season covers the events of Sasuke's Story: Sunrise (サスケ真伝 来光篇, Sasuke Shinden Raikō-hen), Naruto: Shikamaru's Story — A Cloud Drifting in the Silent Dark (NARUTO－ナルト－　シカマル秘伝 闇の黙に浮ぶ雲, Naruto: Shikamaru Hiden — Yami no Shijima ni Ukabu Kumo), and Naruto: Konoha's Story - A Perfect Day For a Wedding (NARUTO－ナルト－　木ノ葉秘伝 祝言日和, Konoha Hiden: Shūgenbiyori).
Meskipun empat episode pertama berkisah tentang masa kecil beberapa karakter utama, bagian lainnya dari musim tersebut mengisahkan peristiwa-peristiwa Sasuke's Story: Sunrise (サスケ真伝 来光篇, Sasuke Shinden Raikō-hen), Naruto: Shikamaru's Story — A Cloud Drifting in the Silent Dark (NARUTO－ナルト－　シカマル秘伝 闇の黙に浮ぶ雲, Naruto: Shikamaru Hiden — Yami no Shijima ni Ukabu Kumo), dan Naruto: Konoha's Story - A Perfect Day For a Wedding (NARUTO－ナルト－　木ノ葉秘伝 祝言日和, Konoha Hiden: Shūgenbiyori).