Students, especially those in Asian regions, are suffering from enormous examination pressure. Recently, this phenomenon extends to examinations not relating to admission for higher studies. This article aims to analyze, from the perspective of the prisoner’s dilemma, the situation of Hong Kong schools that putting much emphasis on Territory-wide System Assessment (TSA). First, this article reviews the interpretations of schools on examination pressure. Then, it analyzes the situation of TSA in Hong Kong with the conception of the prisoner’s dilemma. Finally, it suggests ways to face the dilemma. The author suggests that there may be two approaches to break the dilemma: one is to enhance the rational level of individuals and the other is to change the payoffs of the system. Nevertheless, revising payoffs of the system can change the present situation or the dilemma of the present system, while the new payoff system may cause another dilemma for schools.