The dissertation presents a theoretical synthesis of a problem of education of troubled teenagers during physical trainings. The investigation of a problem is based on the analysis of the sociological, psychological, and pedagogical literature. The dissertation specifies the essence of concepts "troubled teenagers", "personality-oriented approach", "education of moral and volitional qualities". The category of troubled teenagers describes the adolescents who are physically and mentally healthy, however they consciously or unconsciously resist to the pedagogical influence; they also inherent defects of personality development (problems with the adoption of values, formation of moral and volitional qualities) and violate the rules and regulations of behavior that impedes their formation as individuals. The troubled teenagers are in need of personality-oriented approach by teachers, attention of their parents and peers. It has been found that physical trainings possess a strong potential that cannot be realized without specially designed educational technologies aimed at comprehensive education of harmoniously developed personality. One of these technologies is the personality-oriented approach in education. Personality-oriented approach in education of troubled teenagers during the physical trainings could be considered as a system of attitudes towards troubled teenagers during organized pedagogical process of their physical development, which involves respect for the uniqueness and dignity of every personality; the development and formation of natural instincts, personal abilities, values, moral and volitional qualities; the creation of the atmosphere of security, success, support and the provision of troubled teenagers by the principles of humanism, democracy and so on. The implementation of the personality-oriented approach requires the usage of sports-oriented and environmental approaches, the set of which provides the personality of troubled teenager being formed during extracurricular athletic activities. The education of moral and volitional qualities is presented as a result of upbringing, which has been illustrated through assimilation of all vital regulatory and behavioral functions aimed at the personality-valued behaviour, personal subjectivity, creative self-realization and self-improvement. The dissertation has defined the criterion (personality-valued, motivational and volitional, adaptively-subjective, communicative and behavioral), parameters and levels (sufficient, medium, and low) of moral and volitional qualities of troubled teenagers. It has been found that the representative group of troubled teenagers was to be characterized by the levels of education of moral and volitional qualities: 6,75 % respondents of sufficient level, average - 29,85 %, the lowest - 63,4 %. The dissertation theoretically argued and experimentally tested the set of pedagogical conditions of realization of personality-oriented approach in the education of moral and volitional qualities of troubled teenagers in the extracurricular athletic activities, namely: the involvement of troubled teenagers in the sport-orientated organizations; the provision of psychological and methodical preparedness of trainers to educate troubled teenagers of moral and volitional qualities; the usage of innovative forms and methods of personality-oriented education of moral and volitional qualities of troubled teenagers.