Objectives The primary aim of this study was to investigate educational inequalities in health-related exit from paid employment through different pathways in five European regions. A secondary objective was to estimate the proportion of different routes out of paid employment that can be attributed to poor health across educational groups in five European regions. Methods Longitudinal data from 2005 up to 2014 were obtained from the four-year rotating panel of the European Union Statistics on Income and Living Conditions (EU-SILC), including 337 444 persons with 1 056 779 observations from 25 countries. Cox proportional hazards models with censoring for competing events were used to examine associations between health problems and exit from paid employment. The population attributable fraction was calculated to quantify the impact of health problems on labor force exit. Results In all European regions, lower-educated workers had higher risks of leaving paid employment due to disability benefits [relative inequality (RI) 3.3-6.2] and unemployment (RI 1.9-4.5) than those with higher education. The fraction of exit from paid employment that could be attributed to poor health varied between the five European regions among lower-educated persons from 0.06-0.21 and among higher-educated workers from 0.03-0.09. The disadvantaged position of lower-educated persons on the labor market was primarily due to a higher prevalence of poor health. Conclusion In all European regions, educational inequalities exist in health-related exclusion from paid employment. Policy measures are needed to reduce educational inequalities in exit from paid employment due to poor health.