Group mentoring may offer similar supports as traditional one-on-one mentoring and a more culturally consistent forum for addressing issues of ethnicity, academic self-concept and school connectedness (Lindsay-Dennis, Cummings, McClendon, in press; Utsey, Howard & Williams, 2003). The present study investigates the development of students’ ethnic identity, academic self-concept and school connectedness through participation in a school based group mentoring program within a culturally diverse high school. Employing a mixed method design and multilevel modeling analysis, both the ethnicity of the mentor and the diversity composition of each group were assessed as contributors to the mentoring process. Ethnic identity and academic self concept did not yield significant associations (p =.75 and p =.42). School connectedness yielded a significant, but negative association (p < .05) from participation; with multicultural students reporting significantly less connection to the school. Review of process notes maintained by mentors revealed specific group processes that may have influenced the ethnic identity, academic self-concept, and school connectedness of students; such as discussion and resolution of experiences of racism.