Oluwole Joined the Nigerian Army in 1960 and served as part of the United Nations Peacekeeping Force in the Democratic Republic of the Congo.

[3][4] After the war Oluwole Rotimi became the Military Governor of Western State of Nigeria in 1971, under Yakubu Gowon in succession to Brigadier Adeyinka Adebayo.

[7] In 1975, Oluwole Rotimi was removed from office as governor of Western Nigeria after the 1975 coup d'état.

[8] In 1999 Gen. Oluwole Rotimi was appointed by the President Olusegun Obasanjo as the Head of a Commission of Inquiry for the Investigation of Federal Government Landed Property.

In 2005, Oluwole Rotimi was appointed a member of the National Constitutional Review Conference representing his home state-Ogun State.