This paper examines the history of the expansion of educational opportunities in the UK, to understand how different generations of ­working-class students managed to access HE. Based on 23 life-story interviews with working-class students, the study highlights how the changing dynamics of the structure of compulsory education and the labour market have shaped working-class students' views of HE. Exploring the changing structure of opportunity, and how this has shaped working-class students' sense of social position, is key to understanding the uneven pattern of working-class pathways to HE across generations. It is evident that different types of secondary school experience and opportunities in the labour market affected working-class pathways to university with the nature of the school environment and employment shaping various expectations. This article concludes that people's understanding of their social position within the educational and occupational opportunity structure leads to variations in ­working-class transitions to university across different generations.