Itakura Yoshishige served as a bushō in Mikawa Province during the Sengoku period.

Yoshishige was born as the son of Itakura Yorishige. 

Yoshishige was the father of Itakura Katsushige, a daimyō who, in the Edo period, held the role of a magistrate and Kyōto shoshidai, an official of the Edo bakufu in charge of security in Kyōto.

Yoshishige served under Matsudaira Yoshikage of the Fukōzu-Matsudaira family.  In 1561, at the Battle of Zenmyōtsutsumi, he followed Yoshikage to fight against Kira Yoshiaki, but was surrounded by the Kira army and, together with Yoshikage, killed in action.

Yoshishige was succeeded by his third son, Itakura Sadashige.  Sadashige served Tokugawa Ieyasu.  Sadashige  subsequently died during the Siege of Takatenjin Castle so Yoshishige’s second son, Katsushige (who had entered the priesthood at the Eian Temple, the family temple of the Itakura) returned to secular life and inherited the family.  His eldest son, Itakura Tadashige, founded a cadet family and served the Fukōzu-Matsudaira.