This study assessed the level of the implementation of the Obafemi Awolowo University‟s gender policy and identified the challenges encountered in the process. It determined whether the implementation strategy is able to actualize the policy‟s goal of achieving 70:30 male/female participation rates in employment and in leadership positions. The level of staff awareness of the policy was also investigated. Data were derived from in-depth interviews with purposively selected members of staff who were stakeholders in the implementation process of the gender policy such as: past and present Heads of Departments, Deans of Faculties, Provosts of Colleges, and Directors of Institutes and Centers. Secondary data on the status of women in academic and leadership positions were derived from the Planning, Budgeting and Monitoring Unit of the university. This study found that the implementation of the gender policy commenced after its promulgation in 2009 and was sustained for just a couple of years. The process slowed down thereafter due to deeply entrenched patriarchal conservatism, change in the composition of university management that focused less on gender issues, reduced political will, gaps in sensitization and awareness creation of the policy, lack of gender equity network and gender equity implementation committee to facilitate the implementation process, inadequate funds and poor human resource to execute the policy‟s action plans. Also, most Heads of Departments, Deans and other stakeholders did not have copies of the policy and could not utilize it. Lack of effective monitoring and evaluation frameworks were significant implementation challenges. The study concluded that a strong political will as well as a new shift to a more transformative, proactive and nuanced approach by the university stakeholders and management is required to facilitate the implementation of the gender policy.