Sasuke Uchiha features in the alternate universe "Shippū! Konoha Gakuen Den," attending Konoha High School within this high school OVA setting devoid of ninja elements. A prominent student known for his aloof, cool demeanor and signature suit and tie, he instantly forms a fierce rivalry with transfer student Naruto Uzumaki. This rivalry sparks from an accidental kiss during a physical altercation on Naruto's first day, leading to mutual threats and constant competition across various school activities.

Sasuke observes Naruto's violent encounters, including defeating local gang members and challenging top fighters like Kiba Inuzuka, Rock Lee, and Neji Hyūga. Despite their antagonism, Sasuke takes decisive action when the gang leader kidnaps Sakura Haruno, Ino Yamanaka, and Hinata Hyūga for revenge. He leads a rescue group comprising Neji, Kiba, Lee, Shikamaru Nara, Shino Aburame, and Chōji Akimichi, coordinating their efforts to defeat the kidnappers and save Naruto and the girls. This collaboration results in a handshake between Sasuke and Naruto, marking a temporary truce.

Unresolved plot threads involve Sasuke: his hinted connection to Itachi Uchiha, particularly regarding Itachi's association with the Akatsuki organization targeting the school, remains unexplained. Additionally, Sasuke later departs the school with the cross-dressing figures Orochimaru and Kabuto, though his motivations and the circumstances are unclear.