Annaka Kageshige served as a bushō during the Sengoku and Azuchi-Momoyama periods.  Kageshige was the lord of Annaka Castle in Kōzuke Province.

The Annaka clan were kokujin, or provincial landowners, based in the Usui District of Kōzuke Province.

Kageshige was born as the eldest son of Annaka Shigeshige.  Kageshige appears to have received one of the characters in his name from Nagao Kagetora (later known as Uesugi Kenshin) from the period when the Annaka clan served under the Nagao clan (the Uesugi clan of Echigo Province).

In 1563, after the Kai-Takeda clan invaded Kōzuke, Shigeshige resisted from Matsuida Castle while Kageshige defended Annaka Castle.  Kageshige surrendered relatively early in the engagement, so his rights to the castle were recognized by the Takeda, but Shigeshige continued the resistance for a longer period, so, after surrendering, the Takeda seized Matsuida Castle and he was compelled to retire and enter the priesthood leaving Kageshige to inherit the family.

After joining the Takeda clan, Kageshige served under the direction of Amari Nobutada, the chief retainer and a mediator from a multi-generational family of retainers of the Takeda.  Kageshige wed his younger sister.  On 5/21 of 1575, when the Takeda clashed with the Oda at the Battle of Nagashino in Mikawa Province, Kageshige led Annaka forces into battle but was killed in action.  Following his death, Kageshige was succeed by his son, Sakon Taifu.

The members of the Annaka clan participating in the Battle of Nagashino were completely wiped out, with no one from the leader on down returning to Annaka.