Students’ ability to apply mathematical knowledge to various situations has been one of the major concerns in mathematics education research. However, little is known about the assessment strategies that have a substantial contribution to the development of mathematical problem-solving skills in kindergarten children through to upper secondary school students. In this review of existing literature, we discuss the contribution of assessment strategies in the last three decades in strengthening learners’ acquisition of mathematical problem-solving skills. Twenty peer-reviewed conference papers and journal articles published from 1997 to 2020, downloaded from Google Scholar, Academia, and ERIC databases have been analyzed and discussed. Based on this review, it has been noted that the application of assessment strategies such as Structure of the Observed Learning Outcomes taxonomy, Higher-Order Thinking Skills model, performance assessments, authentic assessments, dynamic assessments, and video games-based assessments alongside the learner-centered/active learning methods like problem-based and cooperative learning is bound to strengthen students’ mathematical problem-solving skills.