During the Nanboku-chō period, a local warlord named Kishiwada Osamu was subordinate to Kusunoki Masashige at the Battle of Minatogawa in 1336 and is believed to have built a fortified residence approximately 500 meters southeast of the current castle.

[3] At some unknown point, the castle was relocated to its present site on a small hill at the coastal terrace of Osaka Bay, protected to the north and south by rivers.

Nobunaga seized Kishiwada Castle and placed Oda Nobuharu as castellan to protect against any attempt by the Saiga Ikki and the Ishiyama Hongan-ji armies from linking together.

In 1584, Toyotomi Hideyoshi left the defenses of Osaka undermanned when he marched against Tokugawa Ieyasu to consolidate his position as Nobunaga's successor.

In 1585 the Saiga Ikki armies took advantage of this vacuum to invade Izumi Province, but they were stopped by Hideyoshi's generals Matsuura Munekiyo with Nakamura Kazuuji with 8,000 men at the Battle of Kishiwada.

In order to secure the countryside and to continue to protect Sakai port and his rear flank towards Osaka, Hideyoshi placed his uncle, Koide Hidemasa as castellan and had Kishiwada's defenses strengthened.

The secondary, or "Ni-no-maru" bailey extended in the direction of Osaka Bay, and also had tall stone walls protecting against attack from sea.