Battle of Kawagoe

• Hojo Ujiyasu (8,000) / Hojo Tsunashige (3,000) vs. Uesugi Tomosada / Uesugi Norimasa / Ashikaga Harauji
  • Date: October 1544 – May 1545
  • Location: Musashi province
  • Castle Siege and Battle
  • KIA: Uesugi Tomosada
• Japanese: 河越城の戦い (Kawagoe jô no tatakai)

In an effort to turn back the Hojo expansion into the Kanto, the two branches of the Uesugi (the Yamauchi and Ogigayatsu) allied and, joined by Ashikaga Harauji, besieged Hojo Tsunashige in the strategically important Kawagoe castle. Though two earlier attempts to retake the castle had failed, the allies were encouraged by an alliance between the Takeda clan and Imagawa clan against the Hojo and hoped to take advantage of Ujiyasu's tenuous situation. As long as Ujiyasu was threatened from the west, he could only look on. However, a treaty was reached between the Hojo and Imagawa that allowed Ujiyasu to turn his full attention to Kawagoe, which was slowly being starved out by the allies. After failing to reach a political agreement with the Uesugi, Ujiyasu lead an army into the area and launched a night attack on the Uesugi headquarters that was supported by a spirited sally by Kawagoe's 3,000 defenders. The Uesugi were totally surprised, thrown into confusion, and routed. This brilliant victory was Ujiyasu’s greatest, and one from which neither branch of the Uesugi ever recovered.