The purpose of this study was to discuss the assessment of proficiency in advanced physical skills by focusing on the coaching of the skills for changing running direction under sports settings. In discussion, it was found that the evaluations of the mastery of physical skills could receive a certain level of positive assessment in terms of the presence of mastery but, at the same time, had much room for consideration in respect of the degree of mastery. In addition, it was indicated that the learner’s self-evaluation might be affected by the instructor’s evaluation.