In 1590, He went with Mitsunari to Odawara campaign and was said to have also been present at Oshi Castle, though details of his activities for both conflicts are not clearly listed. When Hideyoshi ordered another suppression of Kii Province, Yoshitsugu was one of the men who participated and caused Akita Sanesue's defeat. He has also been accredited to following Mitsunari through various riots, was a part of creating Fushimi Castle as a fort, and took part in the Korean Campaign (1592-1598). Within the latter conflict, the reputation for his navy was said to be the unparalleled gem of the seas.