In this chapter we analyse the association between employment status and health in Spain at the height of the economic boom (2006) and at the height of the Great Recession (2014). Between these two years unemployment soared to record levels as a result of the world financial crisis. In the context of the theme of the book we focus on workers aged 50 to 69 years. This is an age group which has a higher risk of long-term unemployment as a result of the job loss related to the business cycle (Bentolila et al., 2017), when people transition to retirement and when health often begins to deteriorate (Blau & Gilleskie, 2001). An additional reason for studying this age group is because of the great concern that societies and political agendas have regarding the ageing of the population and the impact this has on pensions and retirement (Diamond, 2007). Lastly, in view of well-known gender differences in both employment trajectories and health status, we take a gender perspective in the analysis and interpretation of the results.