Nakano Naoyoshi served as a bushō during the Sengoku period.  He was a senior retainer of the Ii clan and a kokujin, or provincial landowner, in Iinoya in the Inasa District of Tōtōmi Province.

The Nakano, an illegitimate branch of the Ii clan, was founded by Ii Naofusa, the younger brother of Ii Naouji, the head of the Ii clan.  Naoyoshi was a grandson of Naofusa.  Naoyoshi’s wife (or the wife of his son, Nakano Naoyuki) was the sister of Ohiyo, the wife of Ii Naochika, the head of the Ii clan.

Naoyoshi was a senior retainer of Ii Naomori.  The Ii were subordinate to the Imagawa clan.  In 1560, when Imagawa Yoshimoto, a sengoku daimyō and the eleventh head of the Imagawa, invaded Owari Province, Naomori served with the Imagawa army.  Naoyoshi remained behind to guard Iinoya whereupon Naomori was killed in an attack led by Oda Nobunaga at the Battle of Okehazama.  At the time, Ono Michiyoshi, a senior retainer of the Ii clan, plotted to seize Iinoya so, in his will, Naomori designated Naoyoshi to serve as the guardian of Naomori’s adopted heir, Ii Naochika.  Naochika had poor relations with Michiyoshi.  Upon the direction of Ii Naohira, the prior head of the Ii clan, Naoyoshi was assigned as the guardian of Naochika in accordance with the terms of Naomori’s will.  He then used the name of Shinano-no-kami which had previously been used by Naohira and Naomori.  After Naoyoshi assumed the role as guardian of Naochika, Michiyoshi was unable to assert himself in a despotic manner as desired.  In 1563, Naochika and, in 1564, Naohira, died in succession.  Thereafter, Naoyoshi continued to serve as a guardian of the Ii clan.

In 1564, Inoo Tsuratatsu, the lord of Hikuma Castle, rebelled against the Imagawa clan.  Imagawa Ujizane responded by ordering Naoyoshi, together with Niino Chikanori (a retainer who was close to the Ii clan), to attack Hikuma Castle.  Naoyoshi appealed to the Imagawa clan for additional forces and, with 2,000 reinforcements, launched the attack on the castle.  In the course of a valiant defense by Tsuratatsu and his garrison, Naoyoshi and Chikanori were killed in action on the Tenma Bridge to the east of the castle.  Prior to his demise, Naoyoshi was governing Iinoya so the Ii clan was left without its head.  Following consultations with Yūchinni (the widow of Ii Naomori) and Nankei Zuimon (a priest at the Ryōtan Temple serving as the family temple of the Ii clan), Naomori’s daughter, Jirō-hōshi (Ii Naotora) became the next head of the Ii clan.