There has been limited research on academic tracking and depressive symptoms among high school students in Jamaica. Students enrolled in Grade 10 of traditional and nontraditional high schools in Jamaica were surveyed (N = 278). Students completed the Beck Depression Inventory—II along with several other measures. Seven in every 10 students reported some symptoms of depression. Results of hierarchical regression analyses controlling for social class found that students attending nontraditional high schools reported significantly higher Beck Depression Inventory—II depression scores than students in traditional high schools. This was particularly true for male students attending nontraditional high schools. The strong emphasis on academic achievement and the tracking of students may have a negative association with Jamaican students’ depressive symptoms.