When Hideyoshi attacked Bitchū Takamatsu Castle, Yoshiharu conducted an inquest into the death of Shimizu Muneharu.

Horio killed Saito Toshikazu after he attempt to scroll past Hideyoshi's lines at the Battle of Yamazaki.

Horio Yoshiharu, Nakamura Kazuuji and Ikoma Chikamasa were appointed the three chūrō by Hideyoshi in his last years, and participated in the "Toyotomi administration".

In 1599, he transferred responsibility as head of the family to his son, Horio Tadauji, and was given 50,000 koku as a domain to live after retirement at Fuchu, Echizen Province.

The family temple of the Horio clan is Shunkō-in, in Hanazono, Ukyo District, Kyoto Prefecture.