Shigenaga fought at the Battle of Kawanakajima as rear left wing commander, acting as Uesugi Kenshin's retainer.
The conflict proved costly for Kenshin as Irobe Katsunaga, one of his generals, was slain in the battle and could not take the castle easily.
[5] In 1600, during the conflict between the Toyotomi loyalists, Ishida Mitsunari and Tokugawa Ieyasu, Shigenaga fought in a series of battles once again against Date Masamune and Mogami Yoshiaki at the Siege of Hasedō.
In April 1601, Shigenaga resisted an attack from Date Masamune's warriors at Battle of Matsukawa such as Katakura Kagetsuna, Oniniwa Tsunamoto and Yashiro Kageyori.
Umanosuke struck Shigenaga with the Honjo Masamune which split his helmet, but he survived and took the sword as a prize.