The education system in Jamaica is characterized by differences in the achievements of male and female students. As a follow-up to previous studies conducted in urban Jamaica, this study sought to determine if differences can be observed in the educational achievement at the pre-school level in selected Caribbean countries by examining the competencies of male and female students in Guyana, Jamaica, and St. Vincent and the Grenadines.  Using a mixed methodology, the study also sought to identify factors which impede and facilitate transition to primary school.