Background Syphilis among men who have sex with men (MSM) living with HIV is of public health concern, thus the objective of the study is to determine the correlates of prevalent syphilis infection in this population so that urgent interventions could be instituted. Methods A cross-sectional study was conducted during the period September 2020-June 2021 among MSM who attended a large HIV Clinic in Trinidad. A questionnaire was administered to obtain socio-demographic data and correlates of prevalent syphilis and patients were screened for syphilis using the traditional algorithm. Descriptive and bivariate analyses were conducted and multivariable logistic regression factors was used to assess factors significantly associated with a syphilis diagnosis. Results Two hundred and sixty four MSM were enrolled; age range 18–64 years, median age 33 years and 89 (34.4%) were actively bisexual. The prevalence of syphilis was 28% (74/264) and 89.2% (66/74) of these infections were asymptomatic. Multivariable logistic regression analysis showed that those patients who participated in sex with anonymous partners (OR 2.09; 95% CI, 1.03–4.26), those with a previous diagnosis of syphilis (OR 5.16; 95% CI, 1.03–25.83) and those who used marijuana in the last 12 months (OR 2.13; 95% CI, 1.14–3.96) were more likely to be diagnosed with syphilis. Conclusion There is a high prevalence of asymptomatic syphilis among MSM living with HIV in Trinidad. Repeat episodes of syphilis and anonymous sex may play a role in the transmission dynamics of T pallidum infection in this population, thus urgent public health prevention interventions are warranted.