The present study aimed to identify potential cohort differences in midlife women's self-reported functional limitations and chronic diseases. Additionally, we examined the relationship between marital status and health, comparing the health of divorced, widowed, and never married women with married women, and how this relationship differs by cohort. Using data from the Health and Retirement Study (HRS), we examined potential differences in the level of functional limitations and six chronic diseases in two age-matched cohorts of midlife women in the United States: Pre-Baby Boomers, born 1933-1942, N = 4574; and Early Baby Boomers, born 1947-1956, N = 2098. Linear and logistic regressions tested the marital status/health relationship, as well as cohort differences in this relationship, controlling for age, education, race, number of marriages, length of time in marital status, physical activity, and smoking status. We found that Early Baby Boom women had fewer functional limitations but higher risk of chronic disease diagnosis compared to Pre-Baby Boom women. In both cohorts, marriage was associated with lower disease risk and fewer functional limitations; however, never-married Early Baby Boom women had more functional limitations, as well as greater likelihood of lung disease than their Pre-Baby Boom counterparts (OR = 0.28). Results are discussed in terms of the stress model of marriage, and the association between historical context and cohort health (e.g., the influence of economic hardship vs. economic prosperity). Additionally, we discuss cohort differences in selection into marital status, particularly as they pertain to never-married women, and the relative impact of marital dissolution on physical health for the two cohorts of women.