In the current study, we followed motivational theories and investigated whether granting junior high school students one more opportunity to take the high-stakes high school entrance exam alleviates students' depressive symptoms, and whether the effect is comparable for adolescent boys and girls residing in Taiwan. We analyzed two longitudinal datasets (seventh to tenth grade) from two neighboring cohorts, in which one cohort could take the exam just once (i.e., the pre-reform cohort) and the other twice (i.e., the post-reform cohort). Using a lagged-dependent-variable difference-in-differences model to compare the level of depressive symptoms before and after the entrance exam for the two cohorts, the results revealed that the reform was associated with increases in the level of depressive symptoms for both boys and girls. Despite a higher level of depressive symptoms overall, adolescent girls in the post-reform cohort showed a slower increase in the level of depressive symptoms than boys.