Care leavers, one of the most vulnerable groups in society, are underrepresented in higher education (HE). This study follows 16 entire birth cohorts of alumni of youth villages in Israel (born 1982–1997, N = 44,164) and is based on national administrative data. Using Propensity Score Matching we created a double sized comparison group from the same birth cohorts in the general population (N = 88,328). We use three indicators of educational outcomes: high-school educational attainments, enrollment to HE and HE track. To assess whether attending a youth village is associated with improved outcomes we employ a longitudinal quasi-experimental design and compare the outcomes of care leavers to the matched comparison group. Compared to their matched peers, care leavers were more likely to take at least one matriculation exam and to attain a regular matriculation diploma, but were less likely to gain a diploma that meets the threshold requirement to enter university. Consequently, care leavers were less likely than their matched peers to enroll into HE. Significantly fewer care leavers entered universities, but their rates of entering teachers’ colleges were higher. Our findings suggest that youth villages are relatively successful in terms of high-school achievements. Yet, these are insufficient for care leavers to enter HE and they need further support to bridge the gap with the general population.