Using data from two Toronto student cohorts that entered high school five years apart, this study uses descriptive and multivariate techniques to examine short-term change in the predictors of four possible pathways after high school: confirming a place in university, confirming a place in college, applying but no admittance, or not applying at all. From a comparative cohort perspective, the analysis considers various overlapping ascriptive and school experience factors that contribute to unequal transitions--from race, gender, and immigration background to early achievement, attendance, and suspensions. Even across a short time period, there is change in transition patterns. The results highlight that a comparative cohort approach provides insight into how the transition to post-secondary education in an urban environment changes even over relatively short periods of time.