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Background: Previous research has demonstrated how income-generating activities among marginalized people who use drugs (PWUD)–including employment, income assistance, street-based activities, sex work, and illegal activities–can provide both benefit (e.g., additional income) and harm (e.g., violence, criminalization). However, little is known about gender differences in factors such as drug use patterns that are associated with income-generating activities among PWUD. Methods: Using data from prospective cohorts of HIV-positive and HIV-negative PWUD in Vancouver, Canada, we conducted exploratory gender-stratified analyses of associations between substance use patterns and income-generating activities, using generalized linear mixed-models. Results: Participants reported income sources as employment (23.4 %), income assistance (88.1 %), street-based activities (24.9 %), sex work (15.2 %), drug dealing (31.5 %), or other illegal activities (13.9 %). GLMM results showed gendered patterns of engagement in specific income-generating activities and some diverging patterns of substance use. For instance, men receiving income assistance were less likely to use opioids (Adjusted odds ratio(AOR) = 0.64; 95 % confidence interval(CI) = 0.50–0.82) and women engaged in sex work were more likely to use crack-cocaine (AOR = 2.74, 95 % CI = 2.22–3.37). However, results reflected primarily converging patterns of substance use between women and men across income-generating activities, particularly for drug dealing and other illegal activities. Conclusions: Our results suggest that substance use patterns may be more closely associated with income generation context than gender. Given potential harms associated with some income generation activities, results highlight the need for further investigation of the social and structural context of income generation, its intersections with gender and substance use, and the expansion of low-threshold work opportunities.