[11][12] Ariwoola was born in Iseyin, Oyo State, started his primary education in Local Authority Demonstration School, Oluwole in Iseyin local government area of Oyo State.

He was called to the Nigerian bar and got enrolled at the Supreme Court of Nigeria as a Solicitor and Advocate in July 1981.

He had worked as counsel in the Chambers of Chief Ladosu Ladapo, SAN, between October 1988 and July 1989, when he established Olukayode Ariwoola & Co., a firm of legal practitioners and consultants in Oyo town in August 1989, from where he was appointed in November 1992 as a Judge of Oyo State Judiciary.

He was chairman, Board of Directors, Phonex Motors Ltd., one of the Oodua Investment conglomerates, between 1988 and 1992, and chairman, Armed Robbery Tribunal, Oyo State, between May 1993 and September 1996, when he was posted out of the headquarters, Ibadan, to Saki High Court.

[14][12] In October 2022, Grand Commander of the Order of the Niger (GCON), a Nigerian national honour was conferred on Ariwoola by President Muhammadu Buhari.