Stigma toward same-sex behaviors may be a structural driver of HIV epidemics among men who have sex with men (MSM) in Eastern Europe and has been linked to adverse HIV-outcomes elsewhere. We explored associations between sexual behavior stigma with HIV risk behaviors, testing, treatment, and infection. From November 2017 to February 2018, MSM across 27 Ukrainian cities were recruited to cross-sectional surveys using respondent driven sampling. Eligible participants were cisgender males aged ≥ 14 years residing in participating cities that reported ≥ 1 sexual contact with another man in the prior 6 months. Participants self-reported experience of stigma (ever) and various HIV-outcomes and were tested for HIV antibodies. Regression models were used to explore associations between three sexual behavior stigma variables with demographic and HIV-related variables. Of 5812 recruited cisgender MSM, 5544 (95.4%) were included. 1663 (30.0%) MSM reported having experienced stigma due to being MSM from family and friends, 698 (12.6%) reported anticipated healthcare stigma, and 1805 (32.6%) reported general public/social stigma due to being MSM (enacted). All forms of stigma were associated with heightened HIV risk behaviors; those experiencing stigma (vs not) had more anal sex partners in the prior month and were less likely to have used condoms during their last anal intercourse. Stigma was not associated with HIV infection, testing, or treatment variables. A sizeable proportion of Ukrainian MSM reported ever experiencing stigma due to being MSM. MSM that had experienced stigma had higher odds of HIV sexual risk behaviors. Further study using longitudinal designs is required to determine causality.