Kyoshi was born in what is now the city of Matsuyama, Ehime Prefecture; his father, Ikenouchi Masatada, was a former samurai and fencing master and was also a fan of the traditional noh drama.

Ignoring Shiki's advice, Kyoshi quit school in 1894, and went to Tokyo to study Edo period Japanese literature.

His descendants include his son, the composer, Tomojiro Ikenouchi and great-granddaughter and cellist, Kristina Reiko Cooper.

Kyoshi attached importance to the symbolic function of the kigo (season word), and he tried to exclude the more modern trend towards season-less haiku completely.

This was where Natsume Sōseki's Wagahai wa Neko de aru ("I Am a Cat") was first published, and Kyoshi contributed his own verses and short stories.

As editor of Hototogisu, Kyoshi was instrumental in bringing many new writers and poets into the literary world, including Mizuhara Shuoshi, Yamaguchi Seishi and Takano Suju.