Land degradation in upland areas poses significant environmental and socioeconomic challenges. This study applied the Driver–Pressure–State–Impact–Response (DPSIR) framework to analyze the causal relationships and system dynamics of land degradation in La Libertad, Negros Oriental, with the aim of supporting the integration of Sustainable Land Management (SLM) into local land use planning. The key drivers identified were population growth, steep slope farming, household income levels, and land tenure insecurity—factors that collectively contributed to land cover change. Land cover analysis revealed a major conversion of grasslands to croplands between 2003 and 2015. The state and trends of degradation were assessed using indicators such as land cover transitions, land productivity dynamics, and soil organic carbon levels. Results showed that the most prominent trend was the shift from shrubland and grassland to cropland, leading to increased soil erosion and reduced soil fertility. In response, SLM technologies were implemented, resulting in environmental improvements, including enhanced soil fertility, better land cover, and reduced erosion. Economic benefits included increased agricultural production, higher farm incomes, and improved market access. Socio-cultural impacts involved strengthened decision-making, greater awareness of conservation practices, and improved living conditions. The findings underscore the value of the DPSIR framework as a practical tool for diagnosing land degradation and guiding the mainstreaming of SLM in local land use planning processes.