In 1355 he gathered the army from Shinano Southern Court forces, such as the Suwa clan, the Nishina clan and battled the Military governor of Shinano Province, Nagamoto OGASAWARA at Kikyogahara, however he lost the battle, and returned to Okawara and remained there, to restore the destroyed Southern Court forces in Shinano.
1355年（文和四年/正平十年）諏訪氏・仁科氏など信濃の宮方勢力を結集し、信濃守護小笠原長基と桔梗ヶ原で決戦に及ぶが敗れて、以後は大河原に籠り壊滅した信濃の宮方再建を図る。