This paper studies educational inequality in the Philippines from 1950 to 2015, examining changes in the association between social origin and educational attainment against a backdrop of educational expansions and fluctuating economic conditions. Using data from the World Bank STEP Skills Survey, the study employs a sequential logit model to illustrate trends in secondary and college completion, followed by a multinomial logit model to look into differences in college destinations (type and status) between advantaged and disadvantaged students. The findings indicate that despite sustained expansions in the past six decades, disparities in secondary and tertiary completion deepened in relation to social background. The paper also finds that although expansions occurred mainly in public higher education institutions, it did little to alter the trends in college destinations, with advantaged students still more likely to complete in "high-status" universities than disadvantaged ones. Finally, the paper sheds light on how economic recessions have varying consequences on educational attainment, routing disadvantaged students out of college in the short term, while resulting in significant declines in the likelihood of completing higher education for advantaged students enrolled in "high-status" public entities in the long term.