He ordered that the defenses of the castle be greatly expanded, with a large number of dry moats constructed.

The Hōjō counterattacked as part of an alliance with Takeda Shingen, but as the defenders of the castle were well-prepared, they could not easily retake it.

Shingen brought in sappers from Kai Province in an attempt to undermine the defenses but his also failed.

After three months, Hōjō Ujiyasu tricked the garrison by telling them at they were completely cut off from rescue, as snows has closed the passes to Echigo, and Kenshin's army was forced into winter camp.

At the time of the Odawara Campaign, Toyotomi Hideyoshi sent an army of 40,000 men led by Maeda Toshiie and Uesugi Kagekatsu against Musashi-Matsuyama, and its 2300 defenders surrendered without resistance.