The first well-documented kingdom in what is now southwestern Nigeria was centered at Ife, which was established as the first of the Yoruba kingdoms in the 11th or 12th century. Over the next few centuries, Ife spread their political and spiritual influence beyond the borders of its small city. Ife artisans were highly skilled, producing, among other things, bronze castings of heads in a highly naturalistic style. Terra-cotta, wood, and ivory were also in use at the time.

Shortly after the rise of Ife, the kingdom of Benin emerged. Although it was separate from the Yoruba kingdoms, Benin legends claim that the kingdom's first rulers were descended from an Ife prince. By the 15th century, Benin was a large, well-designed city sustained by trade within the region and, later, with Europeans. Its cultural legacy includes a wealth of elaborate bronze plaques and statues many of which are well known around the world.

At about the same time as Benin's ascendance, the major Yoruba city of Oyo arose. Situated northwest of Ife, Oyo used its powerful cavalry to replace Ife as Yorubaland's political center. Ife, however, continued to serve as the spiritual center of Yorubaland. When the Portuguese first arrived in the late 15th century, it was the Oyo who controlled trade with them, first in goods such as peppers, which they secured from the northern interior lands and transferred to the southern coast, and later in slaves. In Oyo, as elsewhere throughout coastal West Africa, the traffic in slaves had disastrous results. As African nations ventured into the lucrative slave business, conflicts increased, while agricultural and other trades were abandoned. As a result, when the Britain banned slave trade in the early 19th century, Oyo was could not maintain its prosperity. The Oyo state of Ilorin broke away from the empire in 1796 and joined the northern Sokoto caliphate in 1831 after Fulani residing in Ilorin seized power. 
The Oyo empire collapsed, plunging all of Yorubaland Oyo, Ife, and other areas into a bloody civil war that lasted for decades.