Loss of housing and income assistance among vulnerable youth has not been well described in the literature, yet it is a crucial issue for public health. This study examines the prevalence and correlates of loss of income assistance as well as eviction among street-involved youth. We collected data from a prospective cohort of street-involved youth aged 14–26. Among 770 participants, 64.3% reported having housing and 77.1% reported receiving income assistance at some point during the study period. Further, 28.6% and 20.0% of youth reported having been evicted and losing income assistance, respectively. In multivariable generalized estimating equations (GEE) analysis, heavy alcohol use, unprotected sex, being a victim of violence, and homelessness were all independently associated with eviction. Separately, homelessness, recent incarceration, and drug dealing were independently associated with loss of income assistance. Eviction and loss of income assistance are common experiences among street-involved youth with multiple vulnerabilities. Our findings highlight the importance of improving continued engagement with critical social services.