As Takauji went to win the Nakasendai War in 1335 and seceded from the Kenmu Government, Yoshisada was ordered to track down and kill Takauji, which resulted in the defeat of Yoshisada in the Battle of Hakone Take no Shita, so the Ashikaga side approached to Kyoto, but Masashige contacted Akiie KITABATAKE and others to expel the Ashikaga side from Kyoto.
建武2年（1335年）の中先代の乱を討伐に向かった尊氏がそのまま新政に離反し、尊氏追討の命を受けた義貞が箱根・竹ノ下の戦いに敗北して足利軍が京へ迫るが、北畠顕家らと連絡して足利方を京より駆逐する。