As mentoring is receiving increasing attention as a method to improve youth educational outcomes, it is important to continue to examine the effects of mentoring on these youth outcomes. This study uses secondary data from Waves I and III of the National Longitudinal Study of Adolescent Health (Add Health) and transcript data from the Adolescent Health and Academic Achievement Study (AHAA). In seeking support for the compensatory model of resilience, this dissertation uses multiple and logistic regression analyses to examine the direct effects of youth risk factors and the compensatory factor (mentoring) on the educational outcomes: cumulative grade point average (GPA) and graduation from high school. The moderating effects of mentoring on the relationship between youth risk factors and these educational outcomes are also examined. The findings from this study suggest the following characteristics are risk factors for a lower cumulative GPA: younger age, academic risk, racial/ethnic minority status, low maternal education, living with less than both biological parents, lower levels of parental closeness, and lower levels of parental school involvement. On the other hand, only academic risk, low maternal education, and lack of parental participation in school fundraising and volunteering appear to be risk factors for not graduating from high school. Findings also indicate that the compensatory factor, mentoring, is significantly associated with a higher GPA, but is not significantly associated with graduation after controlling for youth risk factors and demographic factors. In support of the protective factor model, two significant moderating relationships were found in terms of predicting graduation between mentoring and the risk factors of living with less than both biological parents and lack of parental participation in school fundraising and volunteering. This study also found that cumulative risk (cumulative risk score was composed of 5 of the risk factors examined) is significantly related to both GPA and graduation, suggesting that youth with more risk factors have worse educational outcomes. The findings of this dissertation add to the existing literature on mentoring and youth educational outcomes. This dissertation's implications for theory, social work, educational practice, policy, and research are discussed as well as this dissertation's strengths and limitations.