In 1582, Hashiba Hideyoshi was ordered to conquer western Japan by Oda Nobunaga and laid siege to Takamatsu Castle.

As Takamatsu Castle was surrounded by marshes, it was considered impregnable to a normal assault and was expected to be able to withstand a prolonged siege.

By paying extravagant amounts of money for round-the-clock efforts, he completed a three-kilometer long dike, damming the outlets to the marshes within 11 days.

Following this siege, and the rise of Toyotomi Hideyoshi to power after the assassination of Oda Nobunaga, the castle became part of the territory of Ukita Hideie, who assigned it to his karō, Hanabusa Masashige.

Takamatsu Castle was featured in the video game Soulcalibur by Namco, used as the fighting stage for the character Heishiro Mitsurugi.