Objective: We investigate whether there are changes over time in years in good health people can expect to live above (surplus) or below (deficit) the pension age, by level of attained education, for the past (2006), present (2018) and future (2030) in the Netherlands. Methods: We used regression analysis to estimate linear trends in prevalence of four health indicators: self-assessed health (SAH), the Organization for Economic Co-operation and Development (OECD) functional limitation indicator, the OECD indicator without hearing and seeing, and the activities-of-daily-living (ADL) disability indicator, for individuals between 50 and 69 years of age, by age category, gender and education using the Dutch National Health Survey (1989–2018). We combined these prevalence estimates with past and projected mortality data to obtain estimates of years lived in good health. We calculated how many years individuals are expected to live in good health above (surplus) or below (deficit) the pension age for the three points in time. The pension ages used were 65 years for 2006, 66 years for 2018 and 67.25 years for 2030. Results: Both for low educated men and women, our analyses show an increasing deficit of years in good health relative to the pension age for most outcomes, particularly for the SAH and OECD indicator. For high educated we find a decreasing surplus of years lived in good health for all indicators with the exception of SAH. For women, absolute inequalities in the deficit or surplus of years in good health between low and high educated appear to be increasing over time. Conclusions: Socio-economic inequalities in trends of mortality and the prevalence of ill-health, combined with increasing statutory pension age, impact the low educated more adversely than the high educated. Policies are needed to mitigate the increasing deficit of years in good health relative to the pension age, particularly among the low educated.