HIV-related stigma can affect health by compromising coping and social support. Gender differences in stigma experiences and social support are underexplored, particularly in the Caribbean. We conducted semi-structured interviews (N = 32) with patients at two HIV clinics in the Dominican Republic. Transcripts were coded using qualitative content analysis (deductive and inductive approaches) to identify themes regarding stigma experiences and social support, which were then compared across men and women participants to identify gender differences. While both men and women described experienced stigma, including verbal abuse, men's experience of stigma were subtler and women described outright rejection and instances of physical violence, including intimate partner violence. Both men and women described job discrimination, but women described severe disempowerment as well as permanent loss of income and/or employment whereas men described temporary changes in employment and /or decrease in income. Men and women described modifying behavior due to anticipated stigma, but only women discussed isolating themselves and discomfort taking HIV medication in front of others. Regarding internalized stigma, both men and women described shame, guilt, and depression over their HIV status, though these experiences were more common among women. Women's experiences prevented health care seeking and included suicidality, while men sometimes blamed women for their HIV status and expressed a desire to "move on" and "look ahead." Both men and women described receiving financial support from family and friends, community support from neighbors, governmental support, and support from other people living with HIV. Women most frequently discussed receiving support from family and friends and using religiosity to cope, whereas men referenced general family support and government benefits and were less forthcoming about personal relationships and social networks, oftentimes not disclosing HIV status to others. The social context of HIV-related stigma affects women and men differently with physical and mental health impacts and may require distinct mitigation approaches.