The evolution of assessment methods and approaches in dental education can be traced through changes in educational systems, advances in educational measurement, and the historical contexts that have shaped their development. Alongside transformations in curricular and pedagogical approaches, assessment methods have continually evolved to meet emerging educational needs. By examining these developments, it is hoped that dental educators have deeper understanding of both the enduring confidence in certain traditional assessment methods and the emergence of newer, more comprehensive approaches. This chapter discusses how the evolving landscape of dental education—from the 1880s to the present—together with advancements in educational measurement, psychology, and the broader historical influences, has shaped assessment practices. It also discusses the foundational concepts and principles of educational measurement that underpin the design and application of assessments in education, thereby assisting dental educators in selecting appropriate methods for evaluating competency within the context of safe dental practice and effective healthcare delivery. The discussion primarily focuses on developments in the United States, given the pivotal roles of the Flexner and Gies reports in formalizing dental education, as well as the global influence of US-led progress in educational psychology, measurement, and standardized testing on education and assessment practices worldwide. Where relevant, the chapter also examines developments in dental education in other countries to provide a more comprehensive and contextualized understanding of global trends.