The cumulative (dis)advantage hypothesis predicts educational differences in health to increase with age. All previous tests of this hypothesis were based on self-reported health measures. Recent research has suggested that self-reported health measures may not adequately capture differences in key analytical constructs, including education, age, cohort, and gender. This article examined the extent to which conclusions about the cumulative (dis)advantage hypothesis depended on the choice of a health measure. The analysis compared self-rated health and the Physical Component Scale as self-reported health measures with grip strength as an objective measure of general physical health. Hierarchical linear models applied to five waves of panel data (SOEP, 2006–2014, N = 3,635 individuals aged 25 to 83, comprising N = 10,385 person-years) yielded two central findings. First, the choice between self-reported and objective health measures strongly influenced conclusions about the cumulative (dis)advantage hypothesis. Second, this influence differed sharply between men and women. For both self-reported health measures, the prediction of the cumulative (dis)advantage hypothesis was consistent with men’s, but not women’s health trajectories. For grip strength, the prediction of the cumulative (dis)advantage hypothesis was consistent with women’s, but not men’s health trajectories.