The XY-Zone program is a leadership and peer support program that guides adolescent males as they journey into manhood. This mixed methods study examined the influence of the XY-Zone program on developmental assets and academic markers of males in grades nine through 12 who were identified as youth at risk of dropping out of school. Results revealed significant positive increases in developmental asset total scores, two asset categories, and two asset contexts. Findings also indicated that youth enrolled in the XY-Zone program improved in academics, behavior, and attendance. Qualitative findings identified four overall positive themes about the XY-Zone program. The XY-Zone program demonstrates promise as an intervention to increase developmental assets of at-risk male youth.