Naomasa was acclaimed for his distinguished war services; though he was a newcomer, he made his name in the Siege of Odawara in 1590 by attacking Odawara-jo Castle at night and being the only commander to breach the castle's defenses.
直政は新参ながら数々の戦功を評価され、天正18年（1590年）の小田原の役では数ある武将の中で唯一夜襲をかけて小田原城内にまで攻め込んだ武将としてその名を天下に轟かせる。