Ujimasa commanded in many battles, consolidating his clan's position, and retired in 1590. His son Hōjō Ujinao became head of the clan and lord of Odawara, but later that year they failed to hold Odawara against the forces of Toyotomi Hideyoshi (see Siege of Odawara (1590)). Ujimasa was forced to commit suicide along with his brother Ujiteru.
- Autumn wind of eve
- Blow away the clouds that mass
- O'er the moon's pure light.
- And the mists that cloud our mind
- Do thou sweep away as well.
(雨雲の おほへる月も 胸の霧も はらひにけりな 秋の夕風)
- Now I'm about to disappear,
- Wondering how I should grasp it.
- From the emptiness I came,
- Hence I will return there.
(我が身今 消ゆとやいかに 思ふべき 空より来たり 空へ帰れば)
- Father: Hōjō Ujiyasu
- Mother: Zuikeiin (d. 1590)
- Ōbaiin (1543–1569), daughter of Takeda Shingen
- Hōshōin (d. 1590)
- Hōjō Shinkurō (1555 – c. 1557) by Ōbaiin
- Hōjō Ujinao by Ōbaiin
- Ōta Gengorō (1563–1582) by Ōbaiin, son-in-law of Ōta Ujisuke
- Ōta Ujifusa (1565–1592) by Ōbaiin, son-in-law of Ōta Ujisuke
- Chiba Naoshige (d. 1627) by Ōbaiin, son-in-law of Chiba Kunitane
- Hōjō Naosada by Ōbaiin
- Hōjō Genzō
- Hōjō Katsuchiyo (b. 1590) by Hōshōin
- daughter married Suzuki Shigeuji
- daughter married Niwata Shigesada
- daughter married Satomi Yoshiyori
- daughter married Chiba Kunitane
In popular culture
Hōjō Ujimasa appears in Koei's video games Kessen, Samurai Warriors 2, Samurai Warriors 3 and Warriors Orochi. He was also in Capcom's Sengoku Basara, Sengoku Basara 2, and Sengoku Basara 2 Heroes as an old man who was armed with spear and has both his ancestral spirits and ice attacks and assisted by Fuma Kotaro. He also appears in The Creative Assembly's Total War: Shogun, and Total War: Shogun 2. Professional wrestler Akito wrestled as Ujimasa for the Dramatic Dream Team promotion on February 10, 2013.