An analysis of the 2012 grade 10 and grade 12 Namibian examination data indicate that girls received higher grades than boys across the then 13 education regions (Educational Management Information System, EMIS, 2012). University of Namibia graduation statistics for the period of 2002 to 2012 revealed that the institution consistently produced graduates in many fields that were more than 60% female (University of Namibia graduation reports of 2002-2012). The Polytechnic of Namibia also produced graduates in various fields for the period of 2006 to 2011 that were more than 60% female (Polytechnic of Namibia graduation reports of 2006-2011). All this is consistent with data from the Southern African Development Community (SADC) region which reveal that Botswana, Mauritius, Namibia, South Africa, Swaziland and Zambia now have a higher proportion of young women than men in tertiary education. SADC data also reveals that Botswana, Lesotho, Namibia, Seychelles, South Africa and Swaziland have 50% or more young women than young men in Secondary School (SADC Gender Protocol Barometer 2013). Similar data were yielded in studies conducted in several Commonwealth countries (Jha and Kelleher 2006). The main purpose of this paper is to explore the manifestations of Namibian boys' underachievement in education by considering various childhood education issues. The first issue is the background to Namibian boys' underachievement in education, the second issue is on the nature and scope of the underachievement in Namibia Primary and Secondary schools, with special reference to boys who underachieve and those who do not. The third issue is on how the phenomenon is manifested in terms of boys' participation and performance in education, enrolment rates, grade repetition rates, school dropout and retention in school, survival rates and promotion rates from grade to grade. The fourth issue focuses on matters pertaining to gender parity in education, boys' socialization and development and social-cultural values that could impinge on boys' performance in education. The firth issue will deal with quality of education, education theory and practice, teacher education and curriculum development implications of Namibian boys' underachievement in education.