Since the coinage of the term ‘wicked problem' in the 1970s, various dimensions of the concept have emerged. Various social ills such as inequality, political instability, terrorism, diseases, famine, poverty, and corruption are considered as wicked problem. Many of the wicked problems are so called because of their complexities and difficulties of finding solutions to the problems. A major wicked problem that is pervasive in many African countries is gender inequality in education. Universal access to education for girls and boys is one of the objectives of the Millennium Development Goals (MDGs). In addition, the Sustainable Development Goals (SDGs) also emphasized quality education and gender equality as two of the main agendas that should be achieved by developed and developing countries. This chapter explores the gender inequality in the educational sector in selected Sub-Saharan African countries. A comparative analysis of the inequality on school enrollment in Kenya, Nigeria, and South Africa was explored. The implication for policy and practice is discussed in this chapter.