The paper describes the digitization of library collections at the Hezekiah Oluwasanmi Library, Obafemi Awolowo University, Ile-Ife in response to the contemporary global trends. The digitization process, one of the earliest in the Nigerian universities, began in 2003 with a focus essentially on abstracts of masters’ dissertations and doctoral theses, as well as newspaper collections of Obafemi Awolowo University, Ile-Ife. The exercise became imperative due to high demand and heavy usage of newspapers and theses by both staff and students for research and learning purposes. The paper further examines the timely intervention of the Carnegie Corporation of New York and partnership with the Association of African Universities on Database of African Theses and Dissertations (DATAD) project based in Accra, Ghana. Challenges being faced include inadequate funding, maintenance of digitization equipment, content management software, capacity building for staff, etc. Challenges notwithstanding, Hezekiah Oluwasanmi Library’s experience has been a win-win situation and its experience will serve as reference points for other sister libraries in the developing world that have joined, and still to join, the bandwagon of digitization train of library collections.