Later in 1560, while Toshiie had been sentenced to prohibition of serving, he took part in the Battle of Okehazama without Nobunaga's permission, and he made achievements of killing enemies and severing three heads in total, one in the morning battle and two in the final battle, but he was not allowed to return to the service for Nobunaga.
その後、永禄3年（1560年）、出仕停止を受けていたのにも関わらず、信長に無断で桶狭間の戦いに参加して朝の合戦で首一つ、本戦で二つの計三つの首を挙げる功を立てるも、帰参は許されなかった。