This study examines sex-specific trends in self-rated health and educational attainment in the United States. We also consider how educational improvements shape trends in self-rated health and whether these associations differ by sex. We draw on 1972-2018 General Social Survey data to extend past research through the recent period when American population health has stalled or declined. Our results show that educational attainment increased throughout the nearly 50-year period, whereas trends in self-rated health were non-linear among both men and women. Among women, self-rated health and education increased together from 1972 to around 2000, but self-rated health declined thereafter even as educational attainment continued to rise. Among men, the association between education and self-rated health was less stable than among women. Education increased, but self-rated health fluctuated over time without a clear trend until the early 2000s. Thereafter, men's self-rated health trended downward. Our findings contribute to a growing body of research showing declines in health status among Americans over recent decades.