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This qualitative study attempts to understand the psychological anatomy of mathematics learners through their thoughts, emotions and behaviours in the context of Singapore education system and society. The main data came from the thought processes, emotional experiences and behaviours that are captured in the reported retrospective memories of 21 polytechnic students with regards to their mathematics learning journey (from young till now) through face-to-face interviews. Six mathematics teachers were also interviewed. The study showed that a student’s internal belief system (consisting of his attitude, motivation and goal) of mathematics learning is influenced by the external expectancy system (expectations of mathematics education set by society, schools, teachers, parents and peers). In explaining the psychological anatomy of mathematics learning, a key stimulus event related to his/her mathematics …