Utilizing financial resources wisely has been one of the education policy objectives to achieve quality education. However, school leaders in their respective school size faced financial management issues that inspired them to utilize financial management strategies. Hence, this study sought to examine their financial management challenges and strategies under the cases of small, medium, large, and mega schools. Six research questions guided the paper which employed phenomenological multiple case study. The sample size of 12 with three school leaders per case in Davao City, Philippines was drawn using the stratified convenience sampling technique. The researchers conducted one-shot in-depth interview and gathered the School Monitoring, Evaluation, and Adjustment (SMEA) document. Employing Colaizzi’s technique and cross-case analysis, the researchers analyzed and clustered responses into themes for single cases which led to the systematic analysis of the multiple cases. Results revealed that school leaders’ financial management challenges involved inadequate staff assistance in small school; delayed release of funds in medium school; high needs and priorities in large school; and difficult Maintenance and Other Operating Expenses (MOOE) liquidation in mega school. In terms of similarities, all cases experienced limited funds and balance and adjustment pressure. Regarding the financial management strategies, school leaders utilized prioritization in small school; prompt liquidation and SMEA in medium school; strict and continuous implementation in large school; and shared governance in mega school. In common, they shared the same strategies which were develop financial plan, ensure transparency, and engage stakeholders. Concerning the financial management insights, they conveyed similar realizations such as competence and honesty. Thus, the theories that governed this study were affirmed. Given these findings, the researchers encouraged school leaders to gain knowledge and improve best practices like financial plan development, transparency, and coordination with stakeholders. DepEd leaders might also consider the enhancement of the MOOE guidelines and policies. Moreover, teaching and non-teaching personnel as well as the stakeholders could take part in financial management through collaboration. Finally, future researchers are encouraged to pursue a related study quantitatively to clearly define the types of strategies that school leaders utilized.