ABSTRACT Leadership has been a topic of intense speculation and controversy for centuries. The quality and effectiveness of leadership is a significant factor in determining the success or failure of an organization. The purpose of this research is to investigate how different leadership styles of musical trainers influence the training effectiveness and the performance of their musical trainees in a wind orchestra. In this research, musical trainers of the Macau Band Directors Association and musical trainees of the Keang Peng Secondary School Wind Orchestra were studied. Tight control experiments with pretest and posttest experimental and control group design were applied to two groups of musical trainees with two trainers who exhibited very different leadership styles. Musical tests of performances were conducted on each musical trainee to obtain their pretest and posttest scores before and after the treatment in order to evaluate the performance of the musical trainees that reflected the training effectiveness and how they were influenced by different leadership styles of the musical trainers. Leadership profiles of the Competing Values Framework were used in this research to measure the relationship between performances of the musical trainees and the leadership styles of the musical trainers. At the conclusion of this study, it was suggested that integration of task-oriented and relationship-oriented leadership styles was necessary for effective musical training in a wind orchestra. This study also suggested ways for a musical trainer in a wind orchestra to improve as a master musical trainer.