Parents of children with significant externalizing and internalizing behavioral problems habitually report greater parenting stress compared to parents of children without these challenges. One avenue to alleviate parenting stress and ameliorate youth outcomes is youth mentoring, which includes a supportive adult paired with a child with the objective of engendering positive outcomes. The researcher sought to (a) evaluate the effectiveness of mentoring programs for children with significant externalizing and internalizing behavioral problems on parenting stress and youth outcomes and (b) explore moderator variables that may influence program effectiveness. Five studies were included in the current meta-analysis. Results revealed a small effect of these specialized mentoring programs on youth outcomes and parenting stress. Moderator analyses revealed program characteristics that enhance effectiveness. Mentoring programs that target children with significant behavioral and emotional problems may function as an additional service to improve youth outcomes and family functioning.