During the Hogen War in July 1156, Masakiyo, who sided with Yoshitomo, fought against MINAMOTO no Tametomo, but retreated because of the enemy's overwhelming power.
保元元年（1156年）7月の保元の乱で義朝に従って従軍し、源為朝に挑むがとても敵わぬと見て退いている。