Poor health after retirement may have an important economic and societal impact and may be affected by macro-level factors. Our aim was to examine whether macro-level factors are associated with health and educational differences in health in recent retirees. We used data covering 18 European countries from the Survey on Health, Ageing and Retirement in Europe (SHARE) and the English Longitudinal Study of Ageing (ELSA) on 8867 respondents who had been retired less than 5 years. We performed multi-level linear regression analyses to examine whether social expenditure in nine policy areas, minimum pension replacement rates, and unemployment replacement rates explained cross-country differences in post-retirement self-rated health (SRH) and educational inequalities in SRH. In both men and women, a higher total expenditure as well as higher expenditures on health, old age, housing, and ‘other social policy areas’ (non-categorical cash benefits to low-income households and other social services) were associated with better SRH. Cross-level interactions showed that in the presence of a higher old age expenditure, a higher unemployment expenditure, and a higher total expenditure, the absolute educational inequalities in post-retirement SRH were smaller than with lower expenditures in these areas, in both men and women. We found the same effect in women only for a higher expenditure on health as well as a higher minimum pension replacement rate. A higher expenditure on survivors pensions, a lower expenditure on family, and a higher unemployment replacement rate had this effect in men only. This study showed that social expenditure and replacement rates were associated with post-retirement health and health inequalities.