The study aimed to assess the practice and challenges of situational leadership styles concerning teachers' readiness levels in primary schools of Wolaita Zone administration. Mixed research design through concurrent strategy was instrumental. A total of 250 teachers and 55 school principals from 20 secondary schools were selected through systematic random and availability sampling techniques respectively to fill out the questionnaire. Besides, 5 senior teachers and 6 secondary school supervisors were interviewed. Both descriptive and inferential statistics are employed to analyze quantitative data, whereas qualitative data is analyzed in narrations. The findings revealed that Wolaita zone administration primary school principals were practicing coaching style under situational leadership style as the dominant style and directing as the second dominant style of leadership. The level of teacher maturity of readiness was fallen into level three as primary and level four as secondary in carrying out the four major teachers' tasks dimensions. The relationship between situational leadership styles and teachers' readiness levels was very weak. It can conclude that most secondary school teachers should focus on supportive behavior and coaching to enhance quality education. It recommends that secondary school principals in the area of study should have to use style three (supportive behavior) as primary and style four as secondary style to serve the needs of teachers. Principals also ought to use style two (coaching) and style one (directing) in the situation when new jobs are introduced and for those teachers newly enter the school system. Long terms and short terms training were recommended to increase leaders' leadership competencies, as well as awareness creation on situational leadership model.