 Okupe worked for some years for government and private hospitals, including St. Nicholas Hospital, Lagos, before establishing the Royal Cross Medical Centre (also known as Royal Cross Hospital) in Obalende, Lagos, along with his colleagues, Dr. Seyi Roberts and Dr. Ladi Okuboyejo.He was the Managing Director (MD) of Royal Cross Medical Centre.According to Olusegun Osoba in a July 2019 interview with The Nation (Nigeria), on the night of 23 August 1994, Okupe and Dr. Seyi Roberts saved the life of his gatekeeper from a gunshot wound to the head.