Technical and vocational education has become a strong focus area for Caribbean countries as they seek to advance their social and economic status in the globally competitive market. Given this context, schools in the Caribbean offer technical and vocational education and training (TVET) subjects to students from various examining bodies. This paper looks at how schools in Jamaica are doing in TVET in the Caribbean Secondary Education Certificate (CSEC) examinations and the leadership and management principles and practices used in administering TVET in selected top performing schools. CSEC data for 41 schools in Jamaica’s Ministry of Education Region One were analyzed for the 2014 examinations, and interviews were conducted in three schools. It was found that while the region did well overall in the TVET subjects, there was a difference in performance by school type; traditional schools outperformed other school types. There was also a strong positive relationship between passes in TVET subjects and passes in English and Mathematics. Various leadership and management practices are used in schools to facilitate TVET, however, results are hampered in part by parents negative mindset towards TVET, and teachers’ limited professional competence. Recommendations are made for dealing with the concerns raised, including increasing students’ literacy and numeracy skills and continued professional development for teachers.