Following his father's death, Yoshitaka assisted the 13th Shogun Yoshiteru ASHIKAGA and Harumoto HOSOKAWA in battles with Nagayoshi MIYOSHI, but the military superiority of this group over the Miyoshi family was reversed and a string of battles were lost.
父の死後も、第13代将軍・足利義輝や細川晴元を助けて三好長慶と戦うが、優勢であった三好家との勢力差が逆転し、敗戦し続けた。