This study aims to disentangle the complex relationships among student attributes, school context, and student performance in mathematics and science in Trinidad and Tobago, using the PISA 2009 data. Our findings reveal that schools account for a substantial amount of variation in students' mathematics and science performances. School socioeconomic status (SES) had a significant effect on student achievement. Additionally, school SES had the single largest effect on mathematics and science achievement among the sample of students of all the explanatory variables. Students who never repeated primary school and who came from two-parent homes outperformed their counterparts on both subjects. Interestingly, females outscored males in science, but there was no significant gender difference in mathematics. These findings suggest the important role of school context in understanding student performance in Trinidad and Tobago and the Caribbean.