1590: He lead the van of the troop of Hidetsugu TOYOTOMI in an expedition against Hojo and captured almost unassisted the main part of the Yamanaka-jo Castle defended by Yasunaga MATSUDA.
天正18年（1590年）：北条征伐において豊臣秀次隊の先鋒を務め、ほぼ単独で松田康長の守る山中城の主要部分を攻略。