Urban youth are an important, yet understudied population. Moreover, the vast majority of existing research has focused on negative outcomes. Recently, there has been a trend in the field of adolescent research toward creating models that attempt to understand and explain why some members of at-risk populations are able to overcome adversities and to achieve successful adaptation. The present study investigated the relationships between perceived social support, gender, academic outcomes, and personal well-being in urban youth. Overall, perceived social support was found to be related to many outcome variables for males and females. Gender differences were found in the relationships between social support and both academic and personal well-being. In particular, the study found that social support was related to girls’, but not boys’ academic outcomes. In terms of personal well-being, results were mixed. The study also examined gender as a possible moderator between types of perceived social support (family, peer, and school) and academic and personal well-being. Results indicated gender did moderate some of the relationships between perceived social support and personal well-being. Lastly, gender differences were found between the relationships between academic achievement and well-being variables, with girls demonstrating more relationships between GPA and personal well-being. These findings are significant in that they highlight the importance of perceived social support and add to the literature attempting to delineate antecedents to positive development in urban youth.