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We assessed the efficacy of a multi-component sexual health promotion program on condom use and human immunodeficiency virus (HIV)/sexually transmitted infection (STI) testing among heterosexual men (HSM) patronizing entertainment establishments who engaged in casual or paid sex in Singapore.This was a quasi-experimental trial with a comparison group using cross-sectional surveys at baseline and 6 months postintervention. A locality patronized by local HSM was assigned the intervention, a comparable and distant area served as the comparison site. Using time location sampling, cross-sectional samples of these men were assessed on sexual behaviors using an anonymous questionnaire at baseline (n = 604) and 6 months postintervention (n = 360) in both groups. The coprimary outcomes were condom use at last vaginal and oral sex with casual partner respectively. Mixed effects Poisson regression model accounting for clustering by establishment was used to compute the adjusted prevalence ratio (aPR) of the outcomes postintervention.At postintervention, the intervention group was more likely than the comparison group to report condom use at last vaginal (aPR, 1.41; 95% confidence interval [CI], 1.05–1.89) and oral (aPR, 1.70; 95% CI. 1.11–2.61) sex, respectively, with casual partner. Similar findings were found for consistent condom use in the last 6 months for vaginal (aPR, 1.67; 95% CI, 1.13–2.48) and oral (aPR, 1.97; 95% CI, 1.16–3.32) sex, respectively, with casual partner. The HIV/STI testing was not significantly higher in the intervention than the comparison group (aPR, 1.43; 95% CI, 0.98–2.09).This trial was effective in promoting condom use with casual partners but not HIV/STI testing among HSM in Singapore.