Understanding determinants associated with dropout from sport is important for talent development. This study aimed (i) to determine dropout rates for Jamaican track and field athletes and (ii) to examine contextual factors (i.e., relative age effect and place of development) as potential determinants of junior athletes progressing to the senior level. A sample of 1552 track and field athletes (mean age 18.57±0.41 years) who were finalists at the national high school (junior) championships in Jamaica between 2000 and 2017 were evaluated from the Jamaica Athletics Administrative Association database. The database provided birth date, school attendance and performance results. A retrospective analysis was completed to investigate the relationship between junior and senior successes and dropout rates. Chi-square analyses were conducted to examine the distribution of birth date quartiles based on the selection year. Using the Jamaican census information, the population size of regions where participants attended school were categorized and used as a proxy for athletes' place of development. Results showed that the majority of the participants did not progress to senior levels (81%). The relative age effect was evident for athletes who progressed to the senior level but was not evident for athletes who did not progress. There was a bias towards participants who attended school in regions with a population size between 5000-29 999. This study illuminates some of the contextual factors that may influence the likelihood of progressing from junior to senior levels which may help to inform talent identification, selection and development in the sport of track and field.