This paper seeks to analyse the validity of the Common Entrance Examination in modern times using qualitative analysis conducted through the lens of human capital and postcolonial theories in the light of male underachievement. This is achieved by highlighting the disparities between genders in achievement and placement in secondary schools based on the Common Entrance Examination.Results indicate that the Common Entrance Examination in Barbados appears to lack validity within the context of the twenty-first century and the issue of male underachievement. This, in turn affects the education system and the pace of national development, which is its aim. The negative effects on human capital have been highlighted, such as the decline in the rate of return to education by men, although equal investment is made to all genders. Further, within the postcolonial analysis the Common Entrance Examination presents itself as merely a symbol of the colonial past, which does not serve the needs of the present society. Suggestions are proffered to deconstruct the hierarchical structure of secondary schools and to eliminate or restructure the examination society to create a more equitable representation of gender parity.