This chapter provides the historical context and development of the Singapore education system. It describes how efforts on teacher professional learning, particularly teachers as our pedagogical leaders, have evolved together with the different emphasis of our developmental phases as a system. The chapter focuses more on teachers’ professional learning in the Student-centred, Values-driven Education Phase (2011–2018) and the current Learn for Life Education Phase (2019–onwards) where teacher learning and professional development focuses on teachers’ career-long development and learning. The chapter also describes efforts to encourage teachers to take ownership of their professional learning and the professional partnerships forged in order to develop teachers along a lifelong professional development continuum.