Meritocracy embodies tension(s) between its egalitarian and elitist strands, which in turn construct how “fairness” is construed in terms of educational opportunity and outcome. In this article, two conflicting notions of fairness are identified, and the dialectic tension and relationship(s) between each are explored. Assessment practices in schools, in particular those pertaining to notions of assessment validity, are identified as early purveyors of merit determination. The case of “holistic assessment” and “bite-sized assessment” in Singaporean primary schools is discussed as an example of the importance of addressing validity in school assessment with the goal of preparing students as future citizens with capacity to fully participate in meritocracy discourse in society. A critical mass of such participative capacity is suggested as an important first step to broaden access to meritocracy, while extending the scope and practice of assessment validity in schools is considered fundamental for developing such capacity.