With the global information boom, and rapid developments in electronic media and the World Wide Web (Web) within the last two decades, the Singapore government envisioned a need for Singapore to be Information Technology (IT) equipped and competent in every industry, beginning most importantly with the education sector. Taking its cue, the Ministry of Education (MOE) implemented rigorous plans for both school teachers and students to possess the necessary skills and knowledge. As a result, there ensued a transformation in existing teaching practices and new expectations of teachers are inadvertently formed. Based on preliminary interviews with practitioners and academics in the area of Education, this paper gives an insight into the changes that have been taking place in the education system in Singapore with respect to the new policies on IT; an overview of the changing roles that teachers have to assume; a brief discussion on how these changes can be expedited, and some possible future trends in the teaching practices and roles of teachers.