This study examined outcomes from a 2-year multi-level, developmental peer-mentoring project. Using quantitative surveys and open-ended qualitative interviews, we examined the perceptions of 1st generation college freshman mentors and high school student mentees from an inner city school. Five overarching themes emerged from the data. Three of the themes related to benefits associated with the developmental mentoring model: 1) benefits of having unstructured meeting time to develop relationships, 2) importance of the duration of the relationship, and 3) utility of having a developmental peer for accessing social capital for college access. The other two themes related to challenges impacting the program: 4) difficulties breaking barriers and, 5) the importance of quality of mentor/mentee matches.