Big Brothers Big Sisters of America (BBBSA) is a non-profit agency that provides mentoring for at-risk, economically disadvantaged youth. Its three objectives include helping youth to improve self-competence, offering encouragement to improve school performance, and fostering youth relationships with family members, peers, and other adults through one-to-one mentoring relationships. In this study, we examined these mentoring relationships, assessing whether gender match types and program types are associated with the developmental areas of school-aged children in the BBBSA program. To measure prot g confidence, competence, and caring, we employed Ragins' model of homogeneity/diversity and utilized multivariate ordinary least square regression with 267 matched pairs from the BBBSA program-based outcome evaluation, Our findings illustrated that same gender matches were negatively associated with competence, second, that cross-gender matches of female mentors/male prot g s showed better competence and caring outcome than a same-gender of female mentors/ female prot g s, third, that same-gender matches of male mentors/male prot g s showed better improvement on caring score than a same match of female mentors/female proteges, and fourth, that community-based programs had significantly higher confidence and caring scores than school-based programs. Implications for practice, policy, and future research are also discussed.