An important dimension of international comparative analysis in education is studying the models of regulation that structure the way in which educational provision is organized. The specialized literature has defined three predominant regulatory models: the traditional bureaucratic professional model, the quasi-market model inspired by neoliberal thought, and the evaluative state model linked to the notion of new public management. This paper seeks to contribute to this line of analysis by studying the evolution of the Chilean education system since 1980. We describe and analyze the models of regulation that have governed Chilean education and their expression in educational reforms and policies; we assert that Chile has adopted all three mentioned models. We also identify some of the principal consequences of these policies: a highly atomized, privatized, and socioeconomically segregated school system; an improvement in access to education and the conditions for the educational process; and an increase in learning outcomes, despite starting from very low levels and stalling during the past decade while remaining highly unequal in character. Thus, we propose some hypotheses to interpret those changes, relating them to the models of regulation as well as the policies previously analyzed. Overall, we affirm that the market and evaluative state models have achieved modest positive effects while producing relevant undesirable consequences. We conclude the paper with a reflection on the character of the particular hybridization of regulatory models developed in Chile, and the types of policy we believe should be prioritized to improve quality, increase innovation, and diminish inequity.