Sociologists of (e)valuation have devoted considerable attention to understanding differences in evaluative practices across a number of fields. Yet, little is understood about how individuals learn about and navigate multivalent valid group styles within a single setting. As a social phenomenon, many accept how central processes of evaluation are to everyday life. Accordingly, scholars have attempted to link research on evaluation to processes of inequality. Nevertheless, the sociology of evaluation only has tenuous, often implicit connections to literature on inequality and disadvantage. This article addresses these two gaps. Drawing on over two hundred hours of ethnographic fieldwork in an urban high school debate league (“League”), twenty-seven semi-structured interviews with League judges, and archival data, we illustrate how high school policy debate judges employ evaluative frames and link them to the implementation of evaluative practices in a disadvantaged setting. We show that the cultural meanings that emerge within the evaluation process—in this case, urban uplift and competition—stem from the conflicted context in which evaluation is occurring. We also make a first step toward applying the conceptual tools within the sociology of evaluation to a disadvantaged setting, and more broadly, suggest that micro-processes of evaluation are important to the study of urban inequality.