Accurate monitoring of oil palm plantations is critical for balancing economic development with environmental conservation in Southeast Asia. However, existing plantation maps often suffer from low spatial resolution and a lack of recent temporal coverage, impeding effective surveillance of rapid land-use changes. In this study, we propose a deep learning framework to generate 10-meter resolution oil palm plantation maps for Indonesia and Malaysia from 2020 to 2024, utilizing Sentinel-2 imagery without requiring new manual annotations. To address the resolution mismatch between coarse 100-meter historical labels and 10-meter imagery, we employ a U-Net architecture optimized with Determinant-based Mutual Information (DMI). This approach effectively mitigates the influence of label noise. We validated our method against 2,058 manually verified points, achieving overall accuracies of 70.64%, 63.53%, and 60.06% for the years 2020, 2022, and 2024, respectively. Our comprehensive analysis reveals that oil palm coverage in the region peaked in 2022 before experiencing a decline in 2024. Furthermore, land cover transition analysis highlights a concerning trajectory of plantation expansion into flooded vegetation areas, despite a general stabilization in rotations with other crop types. These high-resolution maps provide essential data for monitoring sustainability commitments and deforestation dynamics in the region, and the generated datasets are made publicly available at https://doi.org/10.5281/zenodo.17768444.