Siege of Odawara (1590)

Ujimasa held a faint hope that Date Masamune would come to offer support, and if the battle reached a stalemate, Tokugawa Ieyasu would defect to his side.

[1] The massive army of Toyotomi Hideyoshi surrounded the castle in what has been called "the most unconventional siege lines in samurai history."

Included Shimoda fortress at Ise Province led by Chosokabe Motochika, where Hideyoshi's naval forces defeated the Izu suigun.

The Chiba clan, allies of the Hōjō in Shimōsa, also saw Sakura Castle fall to Honda Tadakatsu and Sakai Ietsugu of the Tokugawa army during the campaign.

While the Chiba were consequently divested of all of their holdings, many of their senior members were taken into service by Tokugawa retainer Ii Naomasa, thanks to aid he had received many years earlier from the clan during the occupation of Takeda Katsuyori's Tsutsujigasaki Castle.

[4] However, at Siege of Oshi castle led by Ishida Mitsunari, the defenders surrendered after hearing word that their lord had been defeated at Odawara.