Purpose: The purpose of this study was to examine youth development outcomes in an Urban Squash program. Methods: A mixed method approach to was employed to address three research questions: 1) to what extent did the Urban Squash program exhibit features of a quality OST program?; 2) what aspects of the Urban Squash program were most valued by participants and stakeholders?; and 3) how were outcomes gained within urban squash transferred into the school day. The OST Observation Instrument was employed to provide a measure of fidelity related to the implementation of quality program structures. Youth participants (N = 21) and adults (N = 13) with knowledge of the program were interviewed in a semistructured format. Qualitative inductive analysis and constant comparison methods were used to generate themes. Results: Systematic observations demonstrated that the program reflected a strong program design with activities that were sequenced, active, personally focused, and explicit. Within that context, four qualitative themes related to quality programming include 1) academic enrichment, 2) academic transfer, 3) relationships, and 4) personal and social responsibility. Conclusions: Urban Squash provided a quality program structure. Transfer from the program to the school was evident with academic enrichment and personal and social responsibility.