In Jamaica, where homosexuality is criminalized, scant research has examined associations between sexual stigma and HIV infection. The study objective was to examine correlates of HIV infection among men who have sex with men (MSM) in Jamaica. We conducted a cross-sectional tablet-based survey with MSM in Jamaica using chain referral sampling. We assessed socio-demographic, individual, social, and structural factors associated with HIV infection. A logit-link model, fit using backwards-stepwise regression, was used to estimate a final multivariable model. Among 498 participants (median age: 24, interquartile range: 22–28), 67 (13.5%) were HIV-positive. In the multivariable model, HIV infection was associated with increased odds of socio-demographic (older age, odds ratio [OR]: 1.05, 95% confidence interval [CI]: 1.00–1.10]; residing in Kingston versus Ocho Rios [OR: 6.99, 95% CI 2.54–19.26]), individual (poor/fair versus excellent/good self-rated health [OR: 4.55, 95% CI: 1.81–11.42], sexually transmitted infection [STI] history [OR: 3.67, 95% CI: 1.61–8.38]), and structural (enacted sexual stigma [OR: 1.08, 95% CI: 1.01–1.15], having a health care provider [OR: 2.23, 95% CI: 1.06–4.66]) factors. This is among the first studies to demonstrate associations between sexual stigma and HIV infection in Jamaica. Findings underscore the need to integrate STI testing in the HIV care continuum and to address stigma and regional differences among MSM in Jamaica.