Post-secondary education (PSE) experienced explosive growth and diversification over the past century, affording students a range of increasingly complex pathways that they can travel to acquire a credential. In various jurisdictions, governments have made significant investments to facilitate student uptake of unconventional transfer pathways that involve stops at multiple institutions. But, there has been limited effort to understand the impact of travelling these unconventional pathways on graduate labour market outcomes. Moreover, existing studies across many jurisdictions typically lack access to detailed measures of academic performance, demographics, and other pertinent controls that could explain the relationship between PSE pathway uptake and labour market outcomes. Through this study we model this relationship by drawing on a large custom linkage between student records from the Toronto District School Board (TDSB) and three large administrative datasets housed in Statistics Canada's Education and Labour Market Longitudinal Linkage Platform (ELMLP). This linkage offers census-level coverage of the population of interest and allows us to longitudinally track students from their Grade 9 year at the Toronto District School Board (TDSB), into and through Ontario PSE, and then as they enter the labour market. Our analyses unearth a series of pathway-based earnings disparities that prove robust to available controls. We elaborate on the implications of these findings for policymakers and draw attention to their relevance for scholars interested in school-to-work transitions in Canada and abroad.