Prompt HIV diagnosis decreases the risk of HIV transmission and improves health outcomes. The study objective was to examine rates of delayed HIV diagnosis among non-Latino Black Caribbean immigrants in Florida. The sample included 39,008 Black HIV-positive individuals, aged 13 or older from the Caribbean and the mainland U.S. Delayed HIV diagnosis was defined as AIDS diagnosis within three months of HIV diagnosis. After adjusting for demographic factors, year of HIV diagnosis, transmission mode, neighborhood level socioeconomic status, and rural-urban residence, a disparity persisted for Caribbean-born Blacks in the Bahamas and Haiti compared with U.S.-born Blacks. Male Jamaican-Bahamian-Haitian-born Blacks were more likely to have delayed diagnosis (aOR 2.17, 95% confidence interval [CI] 1.53-3.03; aOR 1.88, 95% CI 1.01-3.44; aOR 1.58, 95%CI 1.58). Findings suggest the need for targeted, culturally relevant interventions to reduce delayed diagnosis incidence among specific Caribbean-born Blacks.