Students' performances in TIMSS have featured strongly in recent discussions and debates about the quality of mathematical learning outcomes both from teachers and policy makers. Findings of TIMSS trends showed that most high school students in Malaysia continue to perform at less than satisfactory levels, particularly, in tasks that are cognitively demanding. In this article, we present a critical analysis of selected TIMSS Tasks and demonstrate how to support students better in the use of Higher Order Thinking Skills ("HOTS") in making progress with such tasks. In so doing we present analyses of TIMSS tasks and a model of these tasks that relate "HOTS," representation and concepts which can be utilised by teachers to understand the role of "HOTS" better in empowering students shift to higher levels of cognitive functioning in the context of tackling TIMSS and similarly demanding tasks. Our analyses and model provide an important starting point for the design of future professional development programs for Malaysian mathematics teachers in reconceptualising "HOTS" and implementing them in regular classrooms.