We examined the relationship between sleep and the affective components of subjective well-being as well as psychological well-being, and between sleep and academic performance, of full-time undergraduate students in a residential college at the National University of Singapore. The aspects of sleep considered were self-reported sleep duration, sleep efficiency, frequency of sleep disturbances, daytime dysfunction, sleep latency and overall sleep quality, as measured by the Pittsburgh Sleep Quality Index. Academic performance was measured using self-reported cumulative average point scores, typically known as grade point average in other institutions. Psychological well-being and the affective components of subjective well-being were assessed using the Flourishing Scale and the Scale of Positive and Negative Experience, respectively. With the exception of sleep latency, our univariate analysis revealed significant associations between the abovementioned facets of sleep, and the affective components of subjective well-being. The analysis also revealed significant associations between the above sleep variables and psychological well-being, except sleep latency and frequency of sleep disturbances. Only daytime dysfunction was found to be significantly correlated with academic performance in our univariate analysis. In addition, our multivariate analysis shows that psychological well-being, affect balance and academic performance each has a direct effect on overall sleep quality. The relationship between overall sleep quality and psychological well-being is U-shaped, while that between overall sleep quality and affect balance is linear and moderated by psychological well-being. The relationship between overall sleep quality and academic performance is either U-shaped or an inverted-U, depending on the level of psychological well-being, which moderates the relationship. These nonlinear relationships indicate that individuals with the highest levels of psychological well-being are not the best sleepers (in terms of overall sleep quality), neither are the highest academic achievers necessarily the best sleepers.