In most developed countries, research studies that investigate the effects of special education on student outcomes have become conventional practice. However, in developing countries such as the twin-island Republic of Trinidad and Tobago, there are no studies about the progress and outcomes of students and youths with disabilities. This correlational study is the first attempt to use direct assessments of English language arts and mathematics, as well as independent functioning skills assessments, aimed at exploring the academic achievement and employment outcomes of 124 participants with and without disabilities in Tobago. The study also compared the performance outcomes of Tobago participants with disabilities with US datasets to see how they measure up in terms of academic achievement and employment. Quantitative analyses of direct assessments and multiple survey responses highlight the factors that predict outcomes in academic achievement and employment among Tobago participants. Findings indicate that parental involvement and support, instruction, student engagement, and support for and difficulty with school work were significant academic achievement predictors for students with disabilities, whereas there were no significant predictors of academic achievement for students without disabilities. The significant predictors of employment for youths with disabilities were parent expectations, teachers' levels of education, youths' school experiences and school program, whereas levels of social interactions with friends, insurance benefits, money skills, types of instruction and types of pre-employment preparation were significant predictors of employment for youths without disabilities. Finally, comparisons with US datasets indicate that Tobago students with disabilities were performing at lower grade levels in academic areas than their US counterparts. Results also found that while Tobago youths with disabilities had fewer employment opportunities than US youths with disabilities, Tobago working youths with disabilities earned higher wages than those youths in the US. These findings highlight the differences between countries in special education practices that present implications for future research on the impact of country policies and programs on outcomes. (Contains 3 figures and 1 table.)