Background: Adolescents living with HIV (ALWH) who transition from pediatric to adult care face several challenges that increase their risk of experiencing treatment interruptions and being lost to HIV care with resultant increased morbidity and mortality. To date, few studies have examined their outcomes post-healthcare transition (HCT), precluding the development and dissemination of evidence-based interventions aimed at retaining ALWH in HIV care both during and after HCT. We conducted a systematic review to synthesize the outcomes of ALWH post-HCT to provide suggestions for future directions. Methods: We systematically searched several electronic databases through October 2019 using keywords for HIV, HCT and ALWH. We categorized studies by target population, country (i.e., upper-high income and low-middle income), study design (i.e., descriptive, mixed methods, quantitative), outcomes measured, and follow-up period. Results: A total of 24 studies met inclusion criteria. Studies were categorized according to the following HCT outcomes: retention in HIV care post-HCT (n = 13), changes in CD4+ count and viral load post-HCT (n = 16), and mortality among ALWH post-HCT (n = 7). Most studies (n = 11) examining retention in HIV care indicated that more than 70% of ALWH were retained in care 1-2 years post-HCT while the remaining studies (n = 2) reported retention rates less than 55%. While studies indicated that CD4+ counts and viral loads tended to worsen during the first few years post-HCT, these differences were often not statistically significant. Among all ALWH who transitioned to adult care, a small proportion died within their first seven years post-HCT. Among qualitative studies, common themes included transition readiness (n = 6), provider-patient relationship in the adult clinic setting (n = 6), and concern about the adult clinic setting (n = 4). Conclusions: Transition outcomes were poorest for ALWH with unsuppressed viremia pre-HCT, suggesting that this subgroup of ALWH may need greater support from their treatment teams and caregivers during and post-HCT to improve clinical outcomes.