Given that the health of many immigrants declines after increasing years in their host countries and that there may be gender differences in these experiences, this exploratory study’s main objective was twofold: a) assess the relationship between acculturative stress and negative health (ie both mental and physical) and b) determine if there were any gender differences in these stress-health relationships. Gender-stratified analyses were conducted on a sample of 418 (males = 158, females = 260) Englishspeaking immigrants (the majority of whom were Jamaicans – males = 81%, females = 86%) that lived in the District of Columbia, Virginia, and Maryland (DC Metropolitan Area, United States of America (USA). Mail-order surveys were used to collect the data over a six-month period in 2002. Data for the main independent variable, acculturative stress, were collected using five indices (ie personal problems, group affiliations, adjustment to life in the USA, lonely feelings and feeling socially satisfied). Data for the major dependent variable, health, were collected using four indices (ie symptoms of depression, physical health conditions, the rating of one’s health and the feeling of control one had over one’s health). After controlling for selected covariates, both males (r = 0.42, p < 0.001) and females (r = 0.19, p < 0.05) reported a positive relationship between personal problems and depression. In other cases, female immigrants, with increasing personal problems, reported more physical health problems (r = 0.20, p < 0.05). Male immigrants who had more group affiliations (r = 0.22, p < 0.05), and who reported more loneliness (r =.26, p < 0.05) had less symptoms of depression. These exploratory results suggest the potential importance of selected variables (eg personal problems and depression) in efforts at improving the health of Caribbean immigrants.