This study examined the relationships between perfectionism, self-esteem, and the will to win and the effects of gender and the level of achievement on these variables. A total of 318 adolescents in the age group of 12–19 years (M = 16.10 ± 1.01) completed the self-esteem questionnaire, the will-to-win questionnaire, and the perfectionism inventory. Interstate level (ISL) athletes obtained higher scores than interdistrict level (IDL) athletes on the following variables: self-esteem, the will to win, and four of the eight dimensions of perfectionism (i.e., concern over mistakes, the need for approval, organization, and planfulness). Further, male athletes obtained higher self-esteem and perfectionism (i.e., the need for approval and rumination) scores than female athletes. Self-esteem, the will to win, and the dimensions of perfectionism were positively and significantly interrelated. However, one dimension, namely, perceived parental pressure, was unrelated to any factor except striving for excellence. Further, the will to win, concern over mistakes, high standard for others, and planfulness were unrelated to striving for excellence. The results of the discriminant analysis revealed that there was no significant difference between ISL and IDL athletes (variance explained = 9.480%). Finally, using path analysis showed that Model 3 (perfectionism self-esteem will-to-win) has provided good model fit such as Bentler's comparative fit index (CFI) (0.987), Tucker-Lewis index (TLI) (0.876), normed fit index (NFI) (0.973), and the root mean square error of approximation (RMSEA) (0.097).