Black men who have sex with men (BMSM) and Black transgender women (BTW) are impacted by dual epidemics of HIV and incarceration. We advanced understanding of the relationship between criminal justice involvement, HIV, and other key HIV-related characteristics among these key populations in the US. We conducted a systematic review up to 2018 and 47 articles met the inclusion criteria of scientific publications involving quantitative findings of US-based HIV-related studies focused on criminal justice-involved (CJI) BMSM and BTW. Overall, there was a dearth of studies focused specifically on BTW. Criminal justice involvement was relatively high among BMSM and BTW and more pronounced among BTW. The current evidence favors no association between incarceration and HIV acquisition among BMSM with limited information about BTW. Criminal justice involvement was associated with a greater likelihood of STIs among BMSM with mixed results for sexual risk behaviors. Criminal justice settings served as an important venue for HIV testing/diagnosis for both BMSM and BTW. However, these settings were not conducive for subsequent stages of the HIV care continuum. Studies pointed to an independent association between criminal justice involvement, substance use, housing instability, and greater odds of incarceration among BMSM who were unemployed and had limited education. Future incarceration was associated with high levels of perceived racism among BMSM. Among young BMSM, high network criminal justice prevalence was also associated with sexual risk behaviors, poorer mental health outcomes, drug use, and housing instability. CJI BMSM and BTW represent a critical subpopulation to end the HIV epidemic in the US.