In 1351, Takauji and his younger brother, Tadayoshi ASHIKAGA, had a conflict between them in the Kanno Disturbance, and Hidetsuna joined together with his father, leading more than three thousand mounted warriors, in the army of Takauji with less than three hundred mounted warriors, which Takauji took up their position in Omi after obtaining an Imperial order to send a punitive force against Tadayoshi,
正平(日本)6年/観応2年（1351年）、観応の擾乱で尊氏とその弟である足利直義が対立し、直義追討の宣旨を得て近江に布陣した三百騎に満たない尊氏の軍に、父と共に三千余騎を率いて真っ先に参じる。