The purpose of this study was to examine the contrasting perceptions of masters swimmers related to the first and fifth constituent years of a 5-year age category. Swimmers aged between 35 and 93 years (154 male, 184 female) were surveyed at the 2008 FINA World Masters Championships. Exploratory factor analysis indicated the existence of the following five factors considered important for preparation, attendance, and success at masters competitions: awareness of advantages, expectancy, motivation, training, and physiological capacity. One sample t-tests showed that masters swimmers are conscious of advantages that 5-year age categories afford to relatively-younger cohorts (i.e., those who are in the first year of any age category). They also perceive that, in the first compared to the fifth year of an age category, they have greater physiological capacity, engage in more training, have higher expectations to perform well, and are more motivated (all ps < .001). Findings point to perceived psycho-social and physical factors that potentially explain why relatively younger masters athletes are more likely to perform better and to participate in masters competitions than relatively older masters athletes.