Bessho Yoshichika served as a bushō of the Bessho clan in eastern Harima Province and as lord of the mountain fortress of Takaoyama Castle.

In 1570, following the death of Yoshichika’s eldest brother, Bessho Yasuharu, Yoshichika joined his younger brother, Bessho Shigemune, to serve as assistants of his nephew, Bessho Nagaharu (the son of Yasuharu). Nagaharu submitted to the Oda after Hashiba Hideyoshi, a senior commanders under Oda Nobunaga, entered Harima. However, Yoshichika clashed with Hideyoshi at a meeting at Kakogawa Castle, and then convinced Nagaharu to rebel against the Oda.  Meanwhile, Shigemune had pledged support for the Oda and became a rōnin, or wandering samurai.

In 1580, Hideyoshi offered as a conditions of surrender that Nagaharu, Bessho Tomoyuki (his younger brother), and Yoshichika commit seppuku in exchange for sparing the lives of the soldiers in the castle. Yoshichika opposed the offer, asserting that he would burn down the castle and turn to himself to ash rather than allow Nobunaga to have his head, whereupon he set fire to his home.  This upset the soldiers defending the castle, who turned upon Yoshichika and killed him, and his head was taken to Nobunaga in Azuchi Castle.  Yoshichika’s wife slayed three children (two sons and one daughter) and then stabbed herself in the throat.  Yoshichika’s eldest son, Bessho Yoshinari, survived and, through his grandson, Bessho Naritada, his descendant named Narimitsu assumed the surname of Isono.