Objectives This study analyzes longitudinal trends in self-rated health (SRH) by taking age-and gender-specific differences into account. Methods Data of 29,251 women and 26,967 men were obtained from the German Socio-Economic Panel between 1995 and 2014. Generalized Estimation Equation analysis for logistic regression was used to estimate changes in odds of (very) good SRH over time. Development of (un)healthy life expectancy was calculated by applying the Sullivan method. Results While in women, the odds of good SRH increased significantly over time for the ages 41-50 to 71-80 years, improvements among men were most apparent for the ages 61-70 and 71-80 years. By contrast, for both genders, no improvements in SRH were found in the youngest (31-40 years) and eldest age group (81-90 years) and in men aging 51-60 years. Over time, healthy life expectancy at age 31 increased by 3 years in women and 2 years in men, leading to a reduced but not eliminated gender gap in SRH. Conclusions Our findings support the hypothesis of relative compression of morbidity. However, trends in SRH differed according to age and gender, calling for health promotion efforts that meet diverse needs at different stages of life.