Takamatsu Castle was founded by Ikoma Chikamasa (1526–1603), who was appointed ruler of Takamatsu by Toyotomi Hideyoshi in 1587. The following year, Chikamasa began construction of the castle on the coast of the Inland Sea (Setonaikai), completing it by 1590.
During the Kamakura period, Sabo Tokitsuna, the sixth son of Sasaki Sadatsuna, built a fort on Mount Sawayama. This fort occupied a strategically important position because it allowed control over traffic along the important Tōsandō route, which was later known as Nakasendō. This road connected the capital, Kyoto, with the eastern regions of the country. Due to its location, the fortification held great military importance, and during periods of civil war it repeatedly became the site of fierce battles.
It is believed that the first structures on this site were built by Tachibana Akitoshi (?-1568), head of the Tachibana clan, a branch family of the Ōtomo clan, as auxiliary fortifications for Tachibanayama Castle. In 1587, Toyotomi Hideyoshi established control over the island of Kyushu and granted Chikuzen Province to Kobayakawa Takakage, one of the leading vassals of the Mori clan. Takakage began construction of a new castle on the site of the existing fortifications in 1588. The exact date of completion is unknown, but by the time the invasion of Korea began in 1592, the castle had already been finished, as records note that Toyotomi Hideyoshi stayed there overnight on his way to Hizen Nagoya Castle, which served as the headquarters of the invasion forces.
The founder of the castle is considered to be Satake Yoshinobu (1570–1633). Yoshinobu was one of the six great generals of Toyotomi Hideyoshi. During the Odawara Campaign of 1590, he took part in the siege of Oshi Castle under the command of Ishida Mitsunari, with whom Yoshinobu developed a good relationship.
Kawanoe Castle is located on the small Wasi-yama hill near the port area of the Kawanoe district in the city of Shikokuchuo, occupying a central position along the northern coast of Shikoku Island. Kawanoe was also known as Butsuden Castle. The term “butsuden” in Japan refers to temple halls, and for this reason it is believed that a Buddhist temple once stood on the site before the castle was built. Due to its location at the junction of four provinces on Shikoku Island, Kawanoe held significant strategic importance and was repeatedly targeted by rival forces seeking military control over the region.
The founder of the castle is considered to be the Onodera clan. The Onodera were originally a minor clan from Shimotsuke Province and served Minamoto no Yoritomo (1147–1199), the founder of the first shogunate. The Onodera distinguished themselves in battle against the Fujiwara clan of the Ōshū branch and were rewarded with lands around Yokote. Around the 14th century, the Onodera moved to Yokote as their permanent residence. Their original stronghold was Numadate Castle, but after a series of clashes with the powerful Nambu clan, they relocated their base to the site of present-day Yokote Castle. It was likely during this time that the first fortifications appeared at the castle.
