(1) The study aim was to assess disparities in non-retention in HIV care and non-viral suppression among non-Hispanic Black Caribbean immigrants living with HIV in Florida. (2) We analyzed cases involving individuals, aged ≥13, who met CDC HIV case definition during 2000-2014. Chi square test was used to evaluate differences in non-retention and non-viral suppression by country of origin/race/ethnicity. Multilevel logistic regressions with three referent groups [US-born Blacks, Hispanics, and non-Hispanic Whites (NHWs)] were used to estimate adjusted odds ratios (aOR). (3) Caribbean-born Blacks were less likely to be retained in care or be virally suppressed than US-born Blacks, Hispanics, and NHWs. Bahamians, Haitians, and Trinidadians and Tobagonians had increased odds of non-retention (aOR 3.13, 95% confidence interval [CI] 2.40 -4.10; aOR 1.52, 95% CI 1.40-1.66; aOR 2.30, 95% CI 1.38-3.83), and non-viral suppression (aOR 3.23, 95% CI 2.48-4.21; aOR 1.82, 95% CI 1.68-1.98; aOR 1.76, 95% CI 1.06-2.90) compared with NHWs. (4) Caribbean-born Blacks living with HIV infection are less likely than other racial/ethnic groups to be retained in care and/or achieve viral suppression. Further research is urgently needed to determine social, cultural, and biological factors that contribute to this disparity.