The 15th – 17th century AD was a period of sociopolitical changes throughout Yorubaland. A critical review of the traditional histories and the results of recent archaeological research in Igbomina reveal that these changes were not restricted to the central Yoruba areas but also manifested in the Yoruba periphery. Ila has been described as a major regional polity in northern Yoruba, whose early development may have followed a similar trajectory as the Old Oyo state. This paper is a report of our recent archaeological survey, excavation, and finds at Ila-Iyara, the major Ila political center occupied between the 14th and 17th centuries. Ila-Iyara exhibits evidence of large elite center, fortifications, sacred sites, iron working, and ceramic types similar to those found at Oyo, Ife, and Benin. The archaeological work in Ila-Iyara also provides further insight into the processes of socio-political development, the dynamics of changes, and the different web of interactions on the Yoruba northern frontier prior to the 18th century.