In 1600, Wakisaka was going to side with
Tokugawa Ieyasu. At this moment, Wakisaka Yasuharu sent his second son, Yasumoto, to march down to Kanto to join the Tokugawa forces punishing
Uesugi Kagekatsu. However, Yasumoto was intercepted by Mitsunari, who had raised an army against Ieyasu, and was forced to return to Osaka from Omi. Yasumoto then sent a letter to Yamaoka Kagetomo, who was accompanying Ieyasu, explaining the situation and conveying his intention to side with Ieyasu. Ieyasu then sent a letter to Yasumoto expressing his gratitude for Yasumoto's loyalty to Ieyasu. He later was compelled to oppose him, siding with
Ishida Mitsunari, who had raised Wakisaka's army when he stayed in Osaka. On October 21, during the decisive
Battle of Sekigahara, Wakisaka switched sides along with
Kobayakawa Hideaki, he defeated
Ōtani Yoshitsugu's force, and contributed to the Tokugawa victory. After the battle, Tokugawa allowed Wakisaka to continue governing his domain of Awaji. In succeeding years, he was given another fief, at Ōzu,
Iyo Province, worth 53,000 koku. His son, Wakisaka Yasumoto, succeeded to the house after his death. ==Popular culture==