The concept and method of mathematics assessment in Singapore schools have undergone some important developments, and in a sense, a paradigm shift, over the last decades. This chapter traces the events and efforts that led to a broadening of the role of student assessment in mainstream Singapore schools and that gave rise to the use of assessment methods other than the “traditional” ones. Beginning with a brief clarification of terms such as tests, examinations, and assessment, the chapter goes on to describe a new conception of assessment and its broader role in the service of student learning. It next compares the so-called alternative and traditional assessment approaches, presents local empirical studies, and highlights critical issues in the design and use of alternative assessment. The chapter ends with some lessons learned, challenges faced, and suggestions for future research in the assessment of mathematics in schools.