- Toyotomi Hideyoshi (200,000) vs. Hojo Ujiyasu/Hojo Ujinao (40,000)
- Date: June - August, 1590
- Location: Sagami province
- Siege
With the defeat of the Shimazu in 1587, only the Hojo remained as a formidable force for Hideyoshi to reckon with. After they refused to pay homage, he invaded the Kanto with an enormous army, spearheaded by Tokugawa Ieyasu. The Hojo, after some heated debate, opted to withdraw the bulk of their forces within the walls of their capital, Odawara - one of the most formidable castles in Japan at that time. There was little actual fighting, as the Hojo hoped that logistical difficulties would force Hideyoshi to call off his siege of their formidable Odawara stronghold. Hideyoshi, however, had made sure that his vast army was well-supplied, and after three months Odawara surrendered. Hojo Ujimasa commited suicide and the Hojo lost the Kanto.