There have been a number of critiques in the last few years of the prevailing paradigm of research on gender and health, which dominated in the latter part of the 20th century. One such criticism has centred on the a historic and decontextualised way in which much evidence for gender differences has been used. In this paper we aim to show that, even within a relatively confined geographical locale over a relatively short period of time, there have been substantial changes in gender relations which are likely to have affected the experience, opportunities, and attitudes of women born in the early 1930s and early 1950s. We illustrate this using data from a study of inequalities in health in Scotland, which includes unusually rich longitudinal data on gender, including occupancy and experience of gender-related roles, attitudinal data on gender equality, and measures of gender role orientation (GRO). These are related to various dimensions of health and health behaviour. The data show substantial differences in the experiences of two generations of women, who are just 20 years apart in age, and a lack of consistency between measures of GRO and health. Whilst on the one hand these data suggest the importance of taking more account of the broader (social, historical or political) context, the analysis also highlights the methodological problems posed.