This paper utilizes administrative data to investigate the gender gap in high school performance on various high-stakes exams and the gender disparity in academic outcomes at the leading university in the Caribbean. The results show that female students outperformed their male peers, being 8.5 and 6.6 percentage points more likely to pass a generic subject in the Caribbean Secondary Education Certificate (CSEC) and Caribbean Advanced Proficiency Examination (CAPE) exams, respectively. These results are robust across subject type, school ownership, school rank, and subject difficulty. In addition, more females are admitted to each degree program annually and continue to outperform males regardless of age, enrollment status, or admission scores. The Blinder-Oaxaca decomposition indicates that school attributes, subject-cohort composition, and subject choice explain up to 78% of the gender gap in CSEC and CAPE pass rates, while college readiness, college-level decisions, and field of study fully explain the gap in college GPA. JEL Classification Codes: I21; I24; J16; J24; N36