Sport has been identified as a context in which youth encounter positive and negative experiences. However, relatively little is known about the factors that lead to positive and negative personal development among sport participants. The purpose of this study was to investigate the role of enjoyment and motivational climate on positive and negative personal development of team sport participants. A sample of 510 athletes between the ages of 9 and 19 completed questionnaires on positive and negative personal development, enjoyment, and motivational climate. Stepwise multiple regression analyses examined the effects of enjoyment and motivational climate on the personal development of the athletes. Results demonstrated that positive experiences in sport were most strongly predicted by affiliation with peers, self-referenced competency, effort expenditure, and a task climate. Negative experiences were most strongly predicted by an ego climate and other-referenced competency. Results suggest that creating an environment that encourages peer affiliation and personal achievement can result in the positive personal development of youth sport participants.