He came from a lineage of warriors and royalty, his father, Olukuoye Ajala was the son of Yamba Bi Ekun, a Bashorun in the Oyo empire during the reign of Alaafin Ojigi. His mother, Agbonrin was the daughter of Alaafin Abiodun I.
Oluyole was a farmer, a blacksmith and later, an armorer. In those days, glory and fame were earned at the battlefield, being the grandson of a warrior, Oluyole set out to become a warrior too, he relocated to Ibadan and within a short period he became the Aareago under Oluyedun (son of Afonja) who was the Baálé of Ibadan after Máyẹ̀ Okunade.
In 1835, Shortly after the death of Lakanle, Oluyole became the Baálé of Ibadan, his new position was challenged when the Fulanis raised one of the largest invasion forces in their history and attacked in a war known as the Eleduwe war. It took a large combined Yoruba army made up of leaders like Kurunmi of Ijaye, Oluyole, and Timi Bamgbaiye of Ede to stop them. Although, the Fulanis were successfully repelled, it was at a great cost to the Òyó empire.
Oyo-Ile, the once mighty seat of one of the largest empires in Africa was destroyed and Alaafin Oluewu, his crown Prince, Adeyanju and his great ally, Eleduwe, the king of the Ibaribas, all perished in the war. Oluyole himself and Prince Atiba nearly lost their lives in the battle.
The survivors moved further south, to Ago d’Oyo or Àgọ Ọja and Atiba was installed as the Alaafin, upon his enthronement, he made Kunrunmi the Aare Ọ̀nà Kakanfo and Oluyole the Bashorun, thereby becoming the first Bashorun of Ibadan. Oluyole took on the challenge of defending the ravaging Ibadan, his reign was bloody, he crushed rebellions both within and outside, his battalion acquired many land that is now part of Ibadan.
He established Ibadan as the military powerhouse on which later leaders build upon. His army emerged victorious in the following wars: Ogun Iberekodo, Ogun Oniyefun, Ogun Oke Bode, Ogun Ẹgbẹ.
Oluyole died in 1850 and Ibadan remains a powerful Yoruba town ever since. His statue stands at Ojà Iba at Béèrè in Ibadan.