This chapter explores mathematics examinations in ancient and present-day Korea and offers some observations on the competitive culture through an analysis of Neo-Confucian philosophy. Findings are illustrated based on oryun, which forms the nexus of the hierarchical social structure that drives examination culture: Students are obligated to abide by the behavioural norms and meet the expectations of parents, siblings, peers, teachers, and other senior members of the society. They exhibit affection and filial piety to parents through excelling in examinations. The obligatory bonds of devotion also include the righteousness to the state in supporting national economic development through acquiring education and technical skills. The examination-oriented learning environments are also related to the differentiation of parenthood in the patriarchal Confucian system, the social order, and the faithfulness between friends. We conclude by discussing the implications of Neo-Confucian learning in understanding mathematical principles, and how they can be practiced and experienced through a reverential way of self-reflection.