This study determined the level of school heads’ managerial skills and teachers’ performance and examined the relationship between these variables in the District of Calatrava I, Division of Negros Occidental. A descriptive-relational research design was employed, involving 243 teachers from 22 elementary schools. Data on school heads’ managerial skills were gathered through a researcher-modified questionnaire based on the Performance Appraisal System for School Heads (PASSH), covering conceptual, human/interpersonal, and technical skills. The instrument obtained an overall validity rating of 4.62, interpreted as Excellent, and a Cronbach’s alpha of 0.970, indicating very high reliability. Teachers’ performance ratings were obtained from the Department of Education’s Individual Performance Commitment and Review Form (IPCRF) for School Year 2015–2016. Results showed that school heads demonstrated managerial competencies in the three areas, although improvement was needed in the implementation of plans, addressing teachers’ needs and weaknesses, and providing technical assistance for curriculum localization and enrichment. Teachers’ performance was generally rated Very Satisfactory. No significant differences were found in school heads’ managerial skills when grouped according to age, sex, civil status, and educational attainment; however, significant differences were found according to length of service across the three managerial skill areas. Moreover, no significant relationship was found between school heads’ managerial skills and teachers’ performance. The study recommends continuous technical assistance, monitoring, classroom observation, and professional development for school heads, particularly in program development, interpersonal and supervisory practices, and curriculum localization and enrichment. Future studies are encouraged to examine other factors that may significantly influence teachers’ performance.