Applying discrete-time hazard models to person-year data constructed from 1% microdata sample of 2010 Korean Census, we explore how men’s education affects their transition to first marriage, and how the relationship between education and marriage has changed across three 10-year birth cohorts of Korean men born from 1946 to 1975. Currently, there is only limited knowledge on how education is related to marriage formation and how the effect is contingent upon macro contexts of education, economy, and family among East Asian men. We find that the high educated delay marriage until later ages but catch up to the extent to which they are eventually more likely to marry than the low educated. There is a continued trend across cohorts toward the delay and avoidance of marriage at all educational levels. However, the trend of retreat from marriage has been more substantial for men with high school or less education compared to men with a university degree, leading to growing educational gaps over time in marriage. We discuss the findings in the contexts of deteriorating economic prospects of Korean men with lower education and also the declining pool of potential spouses for the low educated.