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.