The current study seeks to understand the potential benefits of culturally matched cross-age peer mentoring for Black and Latinx adolescent mentors residing in low-income, urban communities. Data for the study were derived from a 4-year longitudinal project examining the effectiveness of community-based cross-age mentoring. Data from the current sample (N = 249, 60.6% female, M = 16.72 years) were analyzed using HLM. Findings indicated that the mentoring relationship bond rather than attendance predicted change on several positive outcomes. Adolescent mentors were found to experience improvements in several areas of positive youth development, ethnic identity, and GPA after the program was completed and at 9 to 12 months follow up. Researchers propose an adapted theoretical model of the impacts of youth cross-age mentoring in low-income communities of color. Findings from the current study offer key information on the value of facilitating empowering, person-focused services in concert with members of marginalized communities.