Although assigned mentoring relationships have typically involved same-gender matches, a growing number of programs, particularly those in schools, have begun pairing female mentors with male mentees. This practice stems, in large part, from the relative dearth of male mentors and programs' efforts to increase the availability of youth mentoring to young males on waiting lists. We drew on secondary data from the two largest random assignment evaluations of school-based mentoring programs, the Department of Education's Student Mentoring Program and Big Brothers Big Sisters of America's School-based Mentoring, to explore the characteristics and effects of same- versus cross-gender mentoring relationships for male mentees. Our sample included 1,513 male youth from the respective programs. With only a few exceptions, male youth in same- versus cross-gender mentoring relationships experienced similar relationship processes and outcomes. Implications for research and practice are discussed along with limitations including the nonexperimental design of the study and unmeasured effects of selection bias.