This study aimed to investigate the obstacles facing principals in achieving students' scholastic discipline in the Sultanate of Oman according to the principals points of views and to rank these obstacles based on the degree of its occurrence. The study aimed also to disclose the existence of differences among the study sample responses about the degree of the obstacles' occurrence according to the variables of gender, scientific qualification, and years of experience. The study was based on the following questions: 1 - What are the obstacles facing principals in achieving students' scholastic discipline the Sultanate of Oman according to the principals points of views? 2 - Are there statistical significant differences at (a = 0.05) in the responses of the principals regarding the obstacles facing them in achieving students' scholastic discipline, according to the gender, academic qualification, and experience? The study community included a total of (209) male and female principals of basic education schools (5-10) and public education schools (11-12) in three regions in the Sultanate; Muscat, South Batinah, and Eastern North. The study sampled (173) individuals, represented (82.8%) of the study community. This study used a questionnaire as a data collection tool that included (67) items divided into five themes to answer the study questions. The validity of the questionnaire was checked by (15) referees; while reliability was measured using the internal consistency method. The main study results were as follow: 1 - The participants of tlie study ranked descending of the obstacles facing principals in achieving students' scholastic discipline according to the degree of their occurrence as follow: local community related obstacles; students related obstacles; daily school-work related obstacles; teachers and social workers related obstacles, and finally the roles of the school principals related obstacles. 2 - There were no statistical significant differences at the level of significance (a = 0.05) in the responses of the study sample in all the three variables; gender, academic qualifications and experience. The study concluded with some recommendations: rasing parents and local community awareness in issues related to family and community care of school children, creating a commission for students' scholastic discipline in every school; giving school principals more authority regarding students discipline; and organizing programs and training courses for school principals and teachers in how to deal with students' scholastic discipline.