During the Oei War in 1399, he joined his older brother in holding a castle in Sakai City against the army of the bakufu (Japanese feudal government headed by a shogun) led by Shogun Yoshimitsu ASHIKAGA; however his older brother was killed in the attack of the besieging army by setting fire to the castle, and Hiroshige surrendered to Yoshimitsu.
1399年、応永の乱のときに兄に従って堺市に籠城したが、兄が将軍・足利義満率いる幕府軍の火攻めにあって戦死したため、その軍門に降った。