The Philippine school system is considered as one of the largest in the world with 41,989 public elementary and secondary schools and 7790 private schools under the supervision and regulation of the Department of Education (DepEd Fact Sheet, 2005). This paper chronicles various decentralization initiatives carried out by the basic education sector in the country specifically along the areas of education financing, teacher effectiveness, curriculum development, textbooks and instructional materials, and school-community dynamics and student learning and assessment. This discourse culminates with the discussion of the lessons learned from a decentralized system of education for better school operation and management.