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. The results indicated that Jamaican students outperformed their Caribbean counterparts in most of the areas examined. Interestingly, the Early Years Evaluation (EYE) Test showed that, in general, males in all three countries outperformed their female counterparts. The study also revealed that parental, school-related variables and the teaching strategies of teachers are fundamental in facilitating and/or hindering students’ readiness for primary school.