The purpose of this study was to examine the role of homelessness above and beyond the role of poverty alone in contributing to academic and workforce outcomes. Linked longitudinal data from the Maryland Longitudinal Data System (MLDS) and multiple membership multilevel models were used to help disentangle student and school factors to determine the relevant importance of each across a number of outcomes, including high school dropout and graduation, standardized test scores, college enrollment, and annual workforce wages. Academic outcomes for students experiencing homelessness were significantly worse than those for similar, stably housed students experiencing only poverty. Workforce outcomes in terms of total wages earned in the first year after on-time high school graduation were no different for students who had experienced homelessness compared to those who experienced poverty without homelessness. The current study expanded on prior research by distinguishing the roles of poverty and homelessness in relation to longer-term academic and career outcomes. This report also includes policy implications and directions for future research.