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Masashige fought at Battle of Tedorigawa and brought victory to many of his allies, by mobilizing his troops to Etchu and Kozuke. After the death of his previous lord, Uesugi Kenshin, he became quite at odds with the new successor, and son of Kenshin, Uesugi Kagekatsu. Later on he served under Tokugawa Ieyasu, at the Battle of Sekigahara.