This book documents the journey undertaken by educators from the Mathematics and Mathematics Education (MME) Academic Group in the National Institute of Education (NIE) and Singapore schools during a Mathematical Modelling Outreach (MMO) event in June 2010 under the guidance of renowned experts in the field of mathematical modelling. The main goal of MMO was to reach out to Singapore primary and secondary schools and introduce the potentials of mathematical modelling as a platform for eliciting mathematical thinking, communication, and reasoning among students. This book contributes to the expanding literature on mathematical modelling by offering voices from the Singaporean context. It suggests how theoretical perspectives on mathematical modelling can be transformed into actual practice in schools, all within the existing infrastructure of the current Singapore mathematics curriculum. More importantly, the book provides documentary evidence on how plans put in place through MMO in 2010 have since been realised.The publication of this book is hence timely at this juncture. Not only does the book record how MMO was among the first pebbles launched into the pond, it also serves as a bridge over which educators can stand upon to view how the ripple effect had developed from the initial MMO pebble and the directions it may continue to extend. Perhaps in the process, other ripples in the teaching, learning, and research of mathematical modelling can be created.