Objective: HIV prevention programmes such as Jamaica AIDS Support for Life (JASL) work to lower the rate of HIV among marginalized groups. Thus, the objective of this study was to evaluate condom use and HIV status in JASL's SexWorker (SW) population with the intent to identify behavioral differences between this self-selected group and the general SW population in Jamaica. We hypothesized that JASL's SW population would demonstrate higher condom use and a lower prevalence of HIV, potentially attributable to their prevention and education endeavours. Methods: This cross-sectional study (n = 459) uses 2011-2014 data from three cities: Kingston, Montego Bay and Ocho Rios. Data were obtained through voluntary counselling and testing (VCT) forms. Primary outcomes were HIV status and condom use. Frequencies and bivariate analyses were employed. Results: SW HIV prevalence was 1.3%, as compared to the Jamaican SW rate of 4.6%. Most participants reported always using a condom with an outside partner, while only 22% reported always using a condom with their regular partner. Conclusion: Emphasis on condom use within long-term relationships should be considered when planning HIV prevention programmes for SWs. This requires addressing gender roles within noncommercial relationships and more discussions surrounding sexual behaviour outside paid sex work. Although, causality may not be inferred through cross-sectional data, the lower HIV prevalence in JASL's SWs is promising and highlights opportunities for further analysis, specifically around the impact of JASL's work.