David Raffe was a highly influential figure in the field of transitions research. His work carefully delineated how national institutional policies shape transition processes and outcomes. Curriculum structure and organisation were seen as key features of these transition systems, his work tracing the relative impact of vocational and academic qualifications across countries and exploring tendencies towards, and away from, unified qualification frameworks. This paper builds upon David's work by unpacking the influence of curriculum choices in secondary education on young people's labour market destinations in Ireland and Scotland, two countries which share many similarities in their transition and post-16 education systems but differ in the degree of student subject choice at upper-secondary level. Using regression analyses of school leavers' survey data from both countries, we analysed the extent to which subjects studied and grades achieved in secondary school matter for young people's occupational opportunities. We found that subject choice matters for employment chances and access to higher status positions in Scotland but to only a limited extent in Ireland. Grades matter for employment chances in Ireland while higher grades enhance access to higher quality jobs in both countries. The conclusions offer some reflections on David's most recent work and his legacy.