In 1336, his elder brother, Masashige was ordered to fight against the army of Takauji ASHIKAGA who was heading from Kyushu to Kyoto under the command of Yoshisada NITTA, but was defeated in the Battle of Minato-gawa River (Kobe City, Hyogo Prefecture).
1336年（建武7年/延元元年）に兄の正成は九州から京都目指す足利尊氏の軍に対して新田義貞の指揮下で戦う事を命じられ、湊川の戦い（兵庫県神戸市）において戦って敗北する。