In this article, we demonstrate how playful learning serves to provide optimal learning opportunities through teacher-guided play. First, we describe the theoretical design principles that can be leveraged to support mathematical learning for students that have been underserved. Then, we provide concrete examples of evidence-based games that can be directly applied by teachers within their classrooms and beyond the classrooms into the schoolyard. Lastly, we conclude with a detailed graphical tutorial showcasing how the research literature and evidence-based classroom learning activities inform the development of 2 different mathematics games that supplement classroom instruction. We share the design of whole number and rational number basketball games to emphasize how teachers, administrators, and policymakers can replicate these games in their own context. Overall, this work can inform administrators and policymakers on supporting math and physical education by developing guided activities that incorporate the principles of the science of learning, motivation, and physical education science to provide students with optimal math learning opportunities.