Objectives: Exposure to adverse childhood experiences (ACEs) is associated with increased risk of criminal justice involvement and repeated victimization among homeless individuals. This study aimed to (1) examine whether the relationship between cumulative ACE score and odds of experiencing criminal justice involvement and victimization remains significant over time after receiving the Housing First (HF) intervention and (2) investigate the moderating effect of cumulative ACE score on the effectiveness of the HF intervention on the likelihood of experiencing these outcomes among homeless individuals with mental illnesses. Methods: We used longitudinal data over the 2-year follow-up period from the At Home/ Chez Soi demonstration project that provided HF versus treatment as usual (TAU) to homeless adults with mental illness in five Canadian cities (N = 1,888). Results: In all 4 follow-up time points, the relationship between cumulative ACE score and both outcomes remained significant, regardless of study arm (HF vs. TAU) and other confounding factors. However, cumulative ACE score did not moderate intervention effects on odds of experiencing either outcome, suggesting that the effectiveness of HF versus TAU, with regard to the odds of being victimized or criminal justice involvement, did not differ by cumulative ACE scores over the course of study. Conclusions: Findings suggest that providing services for homeless individuals with mental illness should be trauma informed and include specialized treatment strategies targeting the experience of ACEs and trauma to improve their treatment outcomes. An intensive approach is required to directly address the problem of criminal justice involvement and victimization in these individuals.